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[ CAS No. 33904-04-0 ] {[proInfo.proName]}

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Product Details of [ 33904-04-0 ]

CAS No. :33904-04-0 MDL No. :MFCD00041075
Formula : C9H9NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :LHPZZVZPOZPDDB-UHFFFAOYSA-N
M.W : 195.24 Pubchem ID :141856
Synonyms :

Safety of [ 33904-04-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P332+P313+P362+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301+H331-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 33904-04-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 33904-04-0 ]

[ 33904-04-0 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 463-71-8 ]
  • [ 6315-89-5 ]
  • [ 33904-04-0 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine In dichloromethane at 20℃;
88% With sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;
With chloroform; water at 15℃;
  • 2
  • [ 33904-04-0 ]
  • [ 6315-89-5 ]
  • [ 88101-27-3 ]
YieldReaction ConditionsOperation in experiment
83% In acetonitrile at 20℃; Thioureas were prepared according to the reported procedure General procedure: To a solution of aniline (10 mmol) in CH3CN (10 mL) was added isothiocyanate (10mmol). The reation was then stirred until complete conversion of the starting material monitored by TLC. The solvent was removed under reduced pressure and the residue was recrystallized from EtOH to get the desired thioureas 1.
With ethanol
  • 3
  • [ 33904-04-0 ]
  • 2-[1-(4-Nitro-benzyl)-piperidin-4-yl]-ethylamine [ No CAS ]
  • 1-(3,4-Dimethoxy-phenyl)-3-{2-[1-(4-nitro-benzyl)-piperidin-4-yl]-ethyl}-thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% In dichloromethane
  • 4
  • [ 33904-04-0 ]
  • [ 3196-73-4 ]
  • N-(3,4-dimethoxyphenyl)-N'-[(2-methoxycarbonyl)ethyl]thiouree [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With triethylamine In water; acetone at 40℃; for 4h;
In water; acetone for 24h;
  • 5
  • [ 33904-04-0 ]
  • [ 4244-84-2 ]
  • 3-[3-(3,4-Dimethoxy-phenyl)-thioureido]-propionic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With triethylamine In water; acetone at 40℃; for 4h;
  • 6
  • [ 33904-04-0 ]
  • γ-aminobutyric acid isopropyl ester hydrochloride [ No CAS ]
  • 4-[3-(3,4-Dimethoxy-phenyl)-thioureido]-butyric acid isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine In water; acetone at 40℃; for 4h;
In water; acetone for 24h;
  • 7
  • [ 33904-04-0 ]
  • [ 51871-17-1 ]
  • 3-[3-(3,4-Dimethoxy-phenyl)-thioureido]-propionic acid isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine In water; acetone at 40℃; for 4h;
  • 8
  • [4-Chloro-[1,2,3]dithiazol-(5Z)-ylidene]-(3,4-dimethoxy-phenyl)-amine [ No CAS ]
  • [ 33904-04-0 ]
YieldReaction ConditionsOperation in experiment
50% With ethylmagnesium bromide In tetrahydrofuran for 1h; Heating;
  • 9
  • [ 33904-04-0 ]
  • [ 21584-72-5 ]
  • N-(3,4-Dimethoxyphenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinethiocarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In N,N-dimethyl-formamide at 20℃;
  • 10
  • [ 75-15-0 ]
  • [ 6315-89-5 ]
  • [ 33904-04-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: carbon disulfide; 3,4-dimethoxyaniline With triethylamine In toluene at 0℃; for 0.0833333h; Stage #2: With chloroformic acid ethyl ester; triethylamine In chloroform at 20℃; for 2h; Stage #3: With hydrogenchloride In chloroform
100 %Chromat. Stage #1: carbon disulfide; 3,4-dimethoxyaniline With triethylamine In tetrahydrofuran at 20℃; Stage #2: With dmap; di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran at 0 - 20℃; 5 5.1.2. General procedure for the synthesis of isothiocyanates for electron rich aromatic amines (2) General procedure: This procedure was employed to generate corresponding isothiocyanates for final thioureas 3-9 and 14-23. The reverse process,where 1H-indole-5-isothiocyanate was firstly generated followedby subsequent coupling with corresponding amine, was used forfinal thioureas with free phenolic groups (4-7, 17, 19, 21 and 23). An amine (1; 3 mmol) was dissolved in THF (5 mL). While stirring,CS2 (30 mmol, 2.28 g, 1.80 mL) and Et3N (3 mmol, 0.30 g,0.42 mL) were added. After the complete conversion to dithiocarbamic acid salt (monitored via TLC, generally within 30-60 min),the reaction mixture was cooled on an ice bath with immediate addition of Boc2O (2.97 mmol, 0.65 g, 1 mL THF solution) and DMAP (0.03 mmol, 11 mg, 0.5 mL THF solution). Complete consumption of dithiocarbamic acid salt proceeded within 15-60 min. Solvent and other volatiles were removed under reduced pressure yielding isothiocyanate (2) quantitatively (TLC) and used in next step without further purification.
  • 11
  • [ 5739-10-6 ]
  • [ 33904-04-0 ]
  • 1-(2-(1H-imidazol-1-yl)ethyl)-3-(3,4-dimethoxyphenyl)thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.6% In ethanol for 2h; Heating;
  • 12
  • [ 5036-48-6 ]
  • [ 33904-04-0 ]
  • 1-(3,4-dimethoxyphenyl)-3-[3-(1H-imidazol-1-yl)propyl]thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.5% In ethanol for 2h; Reflux;
51.3% In ethanol for 2h; Heating;
51.3% In ethanol for 2h; Heating / reflux; 1; 13 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea EXAMPLE 131-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea4.0 mmol of 3,4-dimethoxyphenyl isothiocyanate and 4.0 mmol of 3-(1H-imidazol-1-yl)alkyl-1-amine were dissolved in 10 mL of absolute ethanol. After stirring for 2 h under reflux, the solvent was evaporated and the resulting solid was recrystallized from ethanol.Yield: 0.66 g (51.3%); mp: 160.0-161.0° C.1H NMR δ 1.8-2.0 (m, 2H), 3.4-3.5 (m, 2H), 3.75 (s, 6H), 3.9-4.0 (m, 2H), 6.7-6.8 (m, 1H), 6.9 (br m, 2H), 6.95 (s, 1H), 7.15 (s, 1H), 7.55 (br s, 1H), 7.6 (s, 1H), 9.3 (s, 1H); MS m/z 321.2 (M+H), 253.3 (M-C3H3N2.)
  • 13
  • [ 33904-04-0 ]
  • [ 112086-54-1 ]
  • 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.5% With triethylamine In ethanol for 2h; Heating;
  • 14
  • [ 33904-04-0 ]
  • [ 67319-76-0 ]
  • 1-(3,4-dimethoxy-phenyl)-3-(4-imidazol-1-yl-butyl)-thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.9% In ethanol for 2h; Heating;
  • 15
  • [ 2067-58-5 ]
  • [ 33904-04-0 ]
  • 1-{4-[bis-(2-chloroethyl)-amino]-phenyl}-3-(3,4-dimethoxyphenyl) thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine In dichloromethane at 20℃; for 36h;
  • 16
  • [ 33904-04-0 ]
  • 1-(3,4-dimethoxyphenyl)-3-[3-(1H-imidazol-1-yl)propyl]thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol 13 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea Example 13 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea 4.0 mmol of 3,4-dimethoxyphenyl isothiocyanate and 4.0 mmol of 3-(1H-imidazol-1-yl)alkyl-1-amine were dissolved in 10 mL of absolute ethanol. After stirring for 2 h under reflux, the solvent was evaporated and the resulting solid was recrystallized from ethanol. Yield: 0.66 g (51.3%); mp: 160.0-161.0° C. 1H NMR δ 1.8-2.0 (m, 2H), 3.4-3.5 (m, 2H), 3.75 (s, 6H), 3.9-4.0 (m, 2H), 6.7-6.8 (m, 1H), 6.9 (br m, 2H), 6.95 (s, 1H), 7.15 (s, 1H), 7.55 (br s, 1H), 7.6 (s, 1H), 9.3 (s, 1H); MS m/z 321.2 (M+H), 253.3 (M-C3H3N2.)
  • 17
  • [ 33904-04-0 ]
  • [ 17356-08-0 ]
  • C10H13N3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: thiourea With sodium hydroxide In acetonitrile at 40℃; for 0.333333h; Stage #2: 4-isothiocyanato-1,2-dimethoxybenzene In acetonitrile at 20℃; for 12h; Further stages.;
  • 18
  • [ 33904-04-0 ]
  • [ 6313-33-3 ]
  • [ 855531-17-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water at 0℃; for 3h; 1.O A mixture of 10 g (51.2 mmol) 4-isothiocyanato-1, 2-dimethoxy benzene in 51 ml THF at 0 °C was treated with 5.1 g (63.3 mmol) formamidine hydrochloride and 63.3 ml IN NaOH and allowed to stirr for 3 h after which the mixture was concentrated. 500 ml ethyl acetate and 100 ml water was added and the precipitate was filtered off and dried to yield the intermediate 1- [1-Amino-methylidene]-3- (3,4-dimethoxy-phenyl)-thiourea (MH+ 240.2) which was used without further purification. The thiourea was taken up in 50 ml THF and treated with 8.55 g (51.2 mmol) ethyl bromoacetate and 14.2 ml NEt3 and stirred at room temperature for 16 h and at 50 °C for 8 h. The mixture was concentrated and extracted with CHCl3. The organic layer was washed with aqueous Na2CO3 (1M) and saturated NaCl solution, dried with MgS04 and evaporated. The residue was purified with reversed phase preparative HPLC to yield 4.04 g (26 %) of the title compound. MS (m/e): 309.2 (MH+, 100%)
  • 19
  • [ 70922-92-8 ]
  • [ 33904-04-0 ]
  • [ 70993-56-5 ]
YieldReaction ConditionsOperation in experiment
In benzene 10 Preparation of 1-benzyloxy-2-[(3,4-dimethyoxphenyl)imino]imidazolidine L-tartrate 8.20 g. of 3,4-dimethoxyphenyl-isothiocyanate are added to a solution of 12.44 g. of N-[2-(benzyloxy)-aminoethyl]phthalimide in 50 ml. of benzene at room temperature. After 36 hours, the precipitate which has formed is filtered off, whereupon 1-benzyloxy-3-(3,4-dimethoxyphenyl)-1-(2-phthalimidoethyl)-2-thiourea, m.p. 120-122°, is obtained.
  • 20
  • [ 109-01-3 ]
  • [ 33904-04-0 ]
  • 4-methylpiperazine-1-(N-3,4-dimethoxyphenyl)carbothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In nitromethane; ethanol 1.a 4-Methylpiperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine STR22 (a) A solution of 3,4-dimethoxyphenyl isothiocyanate (6.8 g., 34.8 mmoles) obtained according to the procedure of G. M. Dyson, et al., J. Chem. Soc., 436 (1927) in 34 ml. of absolute ethanol is added to a stirred solution of N-methylpiperazine (3.49 g., 30.8 mmoles) in 100 ml. of absolute ethanol. After heating the solution to reflux for a 2 hr. period, the solvent is removed under reduced pressure. The semi-solid residue thus obtained is first crystallized from toluene to provide 8.95 g. (87% yield), m.p. 156°-159.5° of the carbothioamide intermediate. Crystallization of this material from nitromethane affords analytically pure 4-methylpiperazine-1-(N-3,4-dimethoxyphenyl)carbothioamide, m.p. 158°-161°. Anal. Calcd. for C14 H21 N3 O2 S: C, 56.92; H, 7.16; N, 14.23; S, 10.85. Found: C, 56.74; H, 7.38; N, 14.40; S, 10.90.
  • 21
  • 1-(5-Methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine hydrochloride [ No CAS ]
  • [ 33904-04-0 ]
  • piperazine-1-(N-3,4-dimethoxyphenyl)carbothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With triethylamine In ethanol 3.a 4-(5-Methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine STR24 (a) 1-(5-Methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine hydrochloride (5.29 g., 0.02 mole) is first added to a stirred solution of triethylamine (2.02 g., 0.02 mole) in 50 ml. of absolute ethanol followed in 5 min. by a solution of 3,4-dimethoxyphenyl isothiocyanate (3.90 g., 0.02 mole) in 15 ml. of absolute ethanol to provide a pale yellow gummy precipitate. The reaction mixture is heated to reflux (during which time the gum crystallizes), diluted with 28 ml. of absolute ethanol, refluxed for an additional 3 hr. period and filtered. The collected material is washed with absolute ethanol and crystallized from methanol to provide 4.41 g. (52% yield) of 4 -methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine-1-(N-3,4-dimethoxyphenyl)carbothioamide, m.p. 143.5°-147°. Anal. Calcd. for C17 H21 N5 O4 S2: C, 48.21; H, 5.00, N, 16.54; S, 15.14. Found: C, 48.28; H, 4.90; N, 16.46; S, 15.19.
  • 22
  • [ 33904-04-0 ]
  • [ 120-35-4 ]
  • 3-[3-(3,4-Dimethoxyphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 72 3-[3-(3,4-Dimethoxyphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.0 mmol), 3,4-dimethoxyphenyl isothiocyanate (0.787 g, 4.0 mmol), and ethyl acetate (25 mL) was heated briefly to 50 C. and then allowed to stand overnight at room temperature. The reaction mixture was diluted with ethyl acetate (~100 mL), heated to 80 C. briefly, then allowed to stand 5 days at room temperature. The precipitate was filtered off to afford the product (0.552 g); m.p. 170-171 C. Calculated for C23H23N3O4S: C, 63.14; H, 5.30; N, 9.60. Found: C, 63.02; H, 5.44; N, 9.58.
  • 23
  • [ 33904-04-0 ]
  • [ 77445-06-8 ]
  • C17H25N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.5% In di-iso-propil ether; acetonitrile at 20℃; for 3h; A4.a A solution of 4-isothiocyanato-l,2-dimethoxybenzene [33904-04-0] (0.16 mol) in DIPE was added to a mixture of 1 -acetyl-4-piperidinemethanamine [77445-06-8] (0.16 mol) in acetonitrile (300ml). The mixture was stirred at room temperature for 3 hours. The solvent was evaporated. The residue was taken up in CHCI3, washed with water, dried (MgSO^, filtered and the solvent was evaporated. The residue was crystallized from CH3OH/DIPE. The precipitate was filtered off and dried, yielding 25.5g (44.5%) of intermediate (8); m.p. 161.3°C.
  • 24
  • [ 33904-04-0 ]
  • [ 1436-59-5 ]
  • C15H23N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In dichloromethane at 20℃; for 24h;
  • 25
  • [ 33904-04-0 ]
  • [ 35132-20-8 ]
  • [ 958936-06-6 ]
YieldReaction ConditionsOperation in experiment
76% In dichloromethane at 20℃; for 17h;
  • 26
  • [ 108038-52-4 ]
  • [ 33904-04-0 ]
  • C17H17N5O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol for 2h; Heating / reflux; 20 5-(1 H-Benzo[d]imidazol-5-yl)-N-(3,4-dimethoxyphenyl)-1 ,3,4-oxadiazol-2-amineIII (0.352g, 2 mmol)) and 3,4 dimethoxyphenylisothiocyanate (0.185g, 2mmol) were dissolved in 20 mL of EtOH and kept under reflux for 2h. After that the solvent was removed and the remaining oil was re-dissolved in 30 mL of THF. After the addition of DCC (1.5 eq) the solution was refluxed for 1 h. The solvent was removed and the remaining oil was purified by means of flash chromatography on AI2O3 utilizing a CHCI3/MeOH gradient.Yield: 0.181 g (27%), MS: m/z 338.2 [M+H]+, HPLC Method [B], (214 nm): rt 9.31 min (95.6%)
  • 27
  • [ 279236-77-0 ]
  • [ 33904-04-0 ]
  • [ 1072801-42-3 ]
YieldReaction ConditionsOperation in experiment
51.4% In ethanol for 2h; Reflux;
40.7% In ethanol for 3h; Heating / reflux; 1 Examples General synthesis descriptionScheme 1 : Synthesis of the thiourea derivatives 1-(3-(5-methyl-1 H-imidazol-1-yl)propyl)-3-arylthioureas Example 1-8, 31The amines or 3-(5-methyl-1 H-imidazol-1-yl)propyl amine (7) (1eq) or 4-(5-methyl-1 H-imidazol-1-yl)butan-1 -amine (8) (1 eq) or 3-(4-methyl-1 H-imidazol-1-yl)propan-1 -amine (12) (1eq) and the corresponding isothiocyanate (1eq) were dissolved in 20 ml. of dry EtOH and the solution was heated under reflux for 3h. The solvent was removed and the products were purified by means of flash-chromatography using silica gel and a CHCI3/MeOH-gradient. Example 1 : 1 -(3,4-dimethoxyphenyl)-3-(3-(5-methyl-1 H-imidazol-1 -yl)propyl)thiourea The compound was synthesized starting from 3-(5-methyl-1 H-imidazol-1 -yl)propyl amine (7)(0.069 g, 0.5 mmol) and 4-isothiocyanato-1 ,2-dimethoxybenzene (0.10 g, 0.5 mmol) as described above.Yield: 0.068 g (40.7%). mp: 139.0-140.0 0C; 1H NMR: (CDCI3) δ 2.01-2.04 (m; 2H); 2.15 (s; 3H);3.62-3.67 (m; 2H); 3.83 (s; 3H); 3.85-3.89 (m; 5H); 6.01 (br s; H); 6.70-6.75 (m; 2H); 6.84-6.86 (m; H); 7.24 (s; H); 7.35 (s; H); 7.72 (s; H); MS: m/z 335.1 (M+H)+; HPLC (λ = 214 nm, [A]) rt:17.20 min (96.0%)
  • 28
  • [ 73866-15-6 ]
  • [ 33904-04-0 ]
  • [ 862821-14-5 ]
YieldReaction ConditionsOperation in experiment
In ethanol for 6h; Heating / reflux; 11 Reagents and conditions: (a) NaH, DMF, 4 h, rt.; (b), 8 h, 100° C.; (c) H2N-NH2,EtOH, 8 h, reflux then 4 N HCl, 6 h, reflux, (d) 3,4 dimethoxy-phenyl-isothiocyanate, EtOH, 6 h, reflux
  • 30
  • [ 2676-33-7 ]
  • [ 33904-04-0 ]
  • [ 1235452-40-0 ]
YieldReaction ConditionsOperation in experiment
70% With lithium perchlorate; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 1.66667h; Reflux;
  • 31
  • [ 147556-16-9 ]
  • [ 33904-04-0 ]
  • [ 1404054-03-0 ]
YieldReaction ConditionsOperation in experiment
63% In N,N-dimethyl-formamide at 20℃; for 48h; Darkness; 18 K2C03 (138mg, lmmol) and 4-isothiocyanato- l,2-dimethoxybenzene (195mg, lmmol) were added sequentially to the solution of curcumin (74mg, 0.2mmol) in DMF (2mL), and the resulting suspension was magnetically stirred at room temperature for a day. After this period, the reaction mixture was allowed to stand for a day in the dark. The formed solid was suction filtered and obtained yellow solid was dried in vacuo (~20mg). Then, filtrate was diluted with water (20mL) and neutralized with 0.5N HCl. The obtained yellow precipitate was extracted with DCM (lOmL X 2). The organic phase was washed with brine, dried and concentrated to give crude which was further subjected to ISCO column chromatography (0-10% CH3OH/DCM) to afford 71 mg yellow solid. Yield was 63% (20mg+51mg).LH519 LH519: 1H NMR (400 MHz, DMSO-d6): δ 2.95 ( dd, 1H, HCH-CHAr), 3.04 ( dd, 1H, HCH-CHAr), 3.69, 3.70 (2 x s, 2 x 3H, 2 x ArOCH3), 3.76 (s, 6H, 2 x ArOCH3), 5.43 (td, 1H, -N-CHAr), 6.72 (dd, J = 8 Hz, 1H, H-c), 6.72 (d, 1H, J = 4 Hz, H-b), 6.86 (d, J = 4 Hz, 1H, H-a), 6.91 (m, 4H, H-2, H-5, H-6, H-b'), 7.14 (dd, J = 8 & 4 Hz, 1H, H-c'), 7.29 (d, J = 4 Hz, 1H, H-a'), 7.58 (s, 1H, CH=C-S), 9.07, 9.77 (2 x s, 2 x 1H, 2 x Ar-OH). 13C NMR (100 MHz, DMSO-d6): δ 44.7 (-COCH2CH-), 55.5, 55.6, 55.7 (3 x ArOCH3), 65.9 (CH2CH-Ar), 105.7 (=C-(C=0)2), 111.1, 11 1.9 (C-2, C-a, C-a'), 115.2, 115.3, 115.5 (C-5, C-b, C-b'), 119.8, 120.0 (C-6, C-c'), 122.5 (C-c'), 124.2, 124.9 (C-q, C-q'), 128.7 (C-l), 130.1 (SC=CH-C(=0)), 133.6 (SC=CH-C(=0)), 146. 4, 147.5, 147.8, 147.9, 148.7, 148.8, 148.9 (3 x C(Ar)-OCH3, 2 x C(Ar)-OH), 177.5 (S(C=)NH), 180.1 (C=0), 182.9 (C=0). MS (ESI+): m/z, 562.01 (M+H).
  • 32
  • [ 33904-04-0 ]
  • [ 83-33-0 ]
  • [ 1421448-24-9 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4-isothiocyanato-1,2-dimethoxybenzene; inden-1-one With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 20℃; for 12h; Stage #2: With hydrazine hydrate; acetic acid In tetrahydrofuran; hexane for 24h; Reflux;
  • 33
  • [ 5650-51-1 ]
  • [ 33904-04-0 ]
  • [ 1469857-35-9 ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: 5,6-dihydro-<6H>-cyclopenta-<b>-thiophene-4-one; 4-isothiocyanato-1,2-dimethoxybenzene With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 8h; Stage #2: With hydrazine hydrate; acetic acid In tetrahydrofuran for 24h; Reflux; 24 Example 24 (4,7-dihydro-1-thia-4,5-diazacyclopenta[a]pentalen-6-yl)(3,4-dimethoxyphenyl)amine A mixture of 5,6-Dihydro-cyclopenta[b]thiophen-4-one (1.0 g, 7.4 mmol) and 4-Isothiocyanato-1,2-dimethoxy-benzene (1.5 g, 7.2 mmol) in THF (2.0 mL) was added to lithium hexamethyl disilane (7.0 mL, 7.2 mmol) dropwise at room temperature. The reaction mixture was stirred for 8 hr. Hydrazine monohydrate (0.4 mL, 7.9 mmol) and glacial acetic acid (0.5 mL) were added to the reaction mixture, which was then heated at the reflux temperature for 24 hr. The resulting mixture was added to water (30 mL) and then extracted with ethyl acetate. The target product was purified by gravity column chromatography (50% EtOAc in hexane) to give (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(3,4-dimethoxy-phenyl)-amine as brown solid in 30% yield. [0237] MS (ESI) m/z: 314.0 (M+H)+. 1H NMR (DMSO-d6): 11.92 (s, 1H), 8.086 (s, 1H), 7.54 (d, 1H), 7.17 (d, 1H), 6.83 (s, 1H), 6.81 (s, 1H), 3.72 (s, 3H), 3.68 (s, 3H), 3.46 (s, 2H).
30% Stage #1: 5,6-dihydro-<6H>-cyclopenta-<b>-thiophene-4-one; 4-isothiocyanato-1,2-dimethoxybenzene With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 8h; Stage #2: With hydrazine hydrate; acetic acid In tetrahydrofuran; water for 24h; Reflux; 24 Example 24(4,7-dihydro-1-thioxo-4,5-diazo-cyclopentadienyl [a] cyclopentan-6-yl) - (3,4-dimethoxy- )-amine A solution of 5,6-dihydro-cyclopenta [b] thiophen-4-one (1.0 g, 7.4 mmol) in THF (2.0 mL)And 4-isothiocyanato-1,2-methoxy-benzene(1.5 g, 7.2 mmol)A solution of lithium hexamethyldisilane was added dropwise at room temperature(7.0 mL, 7.2 mmol). The reaction mixture was stirred for 8 hours. Will monohydrated amine(0.4 mL, 7.9 mmol) and glacial acetic acid (0.5 mL) were added to the reaction mixture and heated at reflux temperature for 24 hours. The product mixture was added to water (30 mL) and extracted with ethyl acetate. Purification by gravity column chromatography (50% EtOAc in hexanes) afforded the title product as a brown solid (4,7-dihydro-1-thi-4,5-diazo-cyclopentadienyl [a] Cyclopentadien-6-yl) - (3,4-dimethoxy-phenyl) -amine in 30% yield.
  • 34
  • [ 5111-70-6 ]
  • [ 33904-04-0 ]
  • N-(3,4-dimethoxyphenyl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% Stage #1: 5-methoxy-1-indanone; 4-isothiocyanato-1,2-dimethoxybenzene With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 12h; Stage #2: With hydrazine hydrate; acetic acid In tetrahydrofuran for 24h; Reflux;
  • 35
  • [ 33904-04-0 ]
  • [ 155252-34-9 ]
  • C31H32N2O9S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With aminosulfonic acid; sodium iodide In acetonitrile at 20℃; Inert atmosphere; A typical procedure for the synthesis of 3-(4-methoxyphenyl)-1-4β-amino podophyllotoxin thiourea (4a) General procedure: To a solution of 4β-azidopodophyllotoxin (3, 100 mg, 0.2 mmol) in acetonitrile (5 mL) was added 4-methoxy phenyl isothiocyanate (37 mg, 0.2 mmol), NaI (38 mg, 0.3 mmol) and NH2SO3H (22 mg, 0.2 mmol). The reaction mixture was stirred for 5-6 hours under nitrogen atmosphere and then neutralized with saturated Na2S2O3 solution. After separation of organic phase, it was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography by employing ethyl acetate/hexane (1:1) as an eluent to give compound 4a (70 mg, 60% yield)
  • 36
  • [ 5192-03-0 ]
  • [ 33904-04-0 ]
  • 1-(3,4-dimethoxyphenyl)-3-(1H-indol-5-yl)thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 20h; 17 5.1.4. General procedure for the synthesis of 1-aryl-3-(1H-indol-5-yl)thiourea (3-23) General procedure: The aromatic amine (1 mmol) was dissolved in DCM (5 mL). Solution of isothiocyanate (1 mmol) in DCM (2 mL) was added drop-wise and the mixture was stirred for 20 h at room temperature. Solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel,CHCl3-MeOH) to yield corresponding product. Compound was recrystallized from Et2O-EtOAc to yield final thiourea.
  • 37
  • [ 33904-04-0 ]
  • [ 107-91-5 ]
  • C12H13N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; Green chemistry; General procedure: Typically, in a 10 mL Initiator reaction vial, phenyl isothiocyanate (1.0 mmol) with cyanoacetamide (1.0equiv) was performed in DMF catalyzed by sodium hydroxide (0.2 equiv) for 30 min at room temperature,
  • 38
  • [ 4097-89-6 ]
  • [ 33904-04-0 ]
  • C15H27N5O2S [ No CAS ]
  • C24H36N6O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃; for 1h; General Procedure for the Preparation of CS-Symmetrical Amine-Urea-Type TAEA Derivatives (12, 13):Example: Synthesis of N-[2-[Bis[2-[(1,3-benzodioxol-5-ylmethyl)amino]ethyl]amino]ethyl]-N′-(tricyclo[3.3.1.13,7]-dec-1-yl)thiourea (12k) (Entry 18) General procedure: (Step 1) To a solutionof TAEA (1, 1.46 g, 10.0 mmol) in CH2Cl2 (160 mL) was added1-adamantyl isothiocyanate (6k, 2.93 g, 15.0 mmol) in CH2Cl2(20 mL) and the mixture was stirred for 1 h at r.t. Evaporationof the solvent gave a pale yellow oil.(Step 2) To a solution of the resulting oil in MeOH (5 mL)was added a solution of piperonal (2d, 3.00 g, 20.0 mmol) inMeOH (10 mL) at r.t. under an argon atmosphere and the mixture was stirred for 20 h.(Step 3) To the resulting yellow solution was addedMeOH (80 mL) and NaBH4 (2.04 g, 54.0 mmol) at 0°C underan argon atmosphere with stirring for 4 h, and then stirring was continued at r.t. for 15 h. After evaporation of thesolvent, aqueous ammonium acetate (NH4OAc, 10%) wasadded to the resulting white solid and the mixture was extracted with CHCl3 (3×200 mL). The separated organic layerwas dried over MgSO4 and filtrated, and evaporation ofthe solvent gave a pale yellow oil. Separation of the products by flash chromatography (CH2Cl2: 95% EtOH : 28%NH3=950 : 47 : 3→73 : 25 : 2) gave 16k (403 mg, 17%) as a whitesolid.
  • 39
  • [ 4097-89-6 ]
  • [ 33904-04-0 ]
  • C33H45N7O6S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 1h; General Procedure for the Preparation of C3-Symmetrical Urea-Type TAEA Derivatives (7, 8): Example:Synthesis of N,N″,N-(Nitrilotri-2,1-ethanediyl)tris[N′-(3,4-dimethoxyphenyl)thiourea] (8l) (Entry 14) To a solutionof 3,4-dimethoxyphenyl isothiocyanate (6l, 2.93 g, 15.0 mmol)in CH2Cl2 (20 mL) was added TAEA (1, 731 mg, 5.00 mmol) atr.t. After stirring for 1 h, the resulting white solid was filtratedto obtain crude compound 8l (3.35 g, 91%). Recrystallizationfrom MeOH gave analytically pure compound 8l as a white solid.8l: mp 161-163°C (from MeOH). IR (KBr) cm-1: 1513(C=S), 1258, 1235, 1134, 1027 (C-O). 1H-NMR (CDCl3) δ:2.67 (6H, t, J=6.9 Hz, H2′), 3.48-3.55 (6H, m, H1′), 3.72 (9H,s, -OCH3), 3.73 (9H, s, -OCH3), 6.79 (3H, dd, J=8.5, 2.1 Hz,H6), 6.90 (3H, d, J=8.5 Hz, H5), 6.96 (3H, d, J=2.1 Hz, H2),7.36 (3H, br s, Hβ), 9.37 (3H, br s, Hα). 13C-NMR (CDCl3)δ: 41.97 (C1′), 52.19 (C2′), 55.45 (-OCH3), 55.70 (-OCH3),109.23 (C2), 111.97 (C5), 116.28 (C6), 131.62 (C1), 146.27 (C4),148.64 (C3), 180.28 (C=S). Positive-ion FAB-MS m/z: 732(M+H+). HR-FAB-MS m/z: 723.2682 (Calcd for C33H46N7O6S3:732.2672). Anal. Calcd for C33H45N7O6S3·0.8H2O: C, 53.10; H,6.29 ; N, 13.14. Found: C, 53.08; H, 6.09; N, 13.22.
  • 40
  • [ 120-57-0 ]
  • [ 4097-89-6 ]
  • [ 33904-04-0 ]
  • N-[2-[bis[2-[(1,3-benzodioxol-5-ylmethyl)amino]ethyl]-amino]ethyl]-N′-(3,4-dimethoxyphenyl)thiourea [ No CAS ]
  • N,N″-[[[2-[(1,3-benzodioxol-5-ylmethyl)amino]ethyl]-imino]di-2,1-ethanediyl]bis[N′-(3,4-dimethoxyphenyl)thiourea] [ No CAS ]
  • 3-(3,4-dimethoxyphenyl)imidazolidine-2-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 45% 2: 22% Stage #1: 2,2',2''-triaminotriethylamine; 4-isothiocyanato-1,2-dimethoxybenzene In dichloromethane at 20℃; for 20h; Stage #2: piperonal In methanol at 20℃; for 20h; Inert atmosphere; Stage #3: With sodium tetrahydroborate In methanol at 0 - 20℃; for 19h; Inert atmosphere; General Procedure for the Preparation of CS-Symmetrical Amine-Urea-Type TAEA Derivatives (12, 13):Example: Synthesis of N-[2-[Bis[2-[(1,3-benzodioxol-5-ylmethyl)amino]ethyl]amino]ethyl]-N′-(tricyclo[3.3.1.13,7]-dec-1-yl)thiourea (12k) (Entry 18) General procedure: (Step 1) To a solutionof TAEA (1, 1.46 g, 10.0 mmol) in CH2Cl2 (160 mL) was added1-adamantyl isothiocyanate (6k, 2.93 g, 15.0 mmol) in CH2Cl2(20 mL) and the mixture was stirred for 1 h at r.t. Evaporationof the solvent gave a pale yellow oil.(Step 2) To a solution of the resulting oil in MeOH (5 mL)was added a solution of piperonal (2d, 3.00 g, 20.0 mmol) inMeOH (10 mL) at r.t. under an argon atmosphere and the mixture was stirred for 20 h.(Step 3) To the resulting yellow solution was addedMeOH (80 mL) and NaBH4 (2.04 g, 54.0 mmol) at 0°C underan argon atmosphere with stirring for 4 h, and then stirring was continued at r.t. for 15 h. After evaporation of thesolvent, aqueous ammonium acetate (NH4OAc, 10%) wasadded to the resulting white solid and the mixture was extracted with CHCl3 (3×200 mL). The separated organic layerwas dried over MgSO4 and filtrated, and evaporation ofthe solvent gave a pale yellow oil. Separation of the products by flash chromatography (CH2Cl2: 95% EtOH : 28%NH3=950 : 47 : 3→73 : 25 : 2) gave 16k (403 mg, 17%) as a whitesolid, 13k (365 mg, 6%) as a white solid, and 12k (2.03 g, 33%)as a colorless semisolid.
  • 41
  • [ 33904-04-0 ]
  • [ 53386-64-4 ]
  • 1-benzyl-3-(3,4-dimethoxyphenyl)-2-sulfanylideneimidazolidin-4-one [ No CAS ]
  • 42
  • [ 33904-04-0 ]
  • [ 71704-67-1 ]
  • 4-(3,4-dimethoxyphenyl)-1-(4-methylimidazol-5-oyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In ethanol Reflux; 3.2. General Procedure for Synthesis of the Imidazole-Thiosemicarbazides 2-22 General procedure: A solution of 4-methylimidazole-5-carbohydrazide (0.01 mol) and an equimolar amount of an isothiocyanate (0.01 mole) in anhydrous ethanol (25 mL) was heated under reflux for 10-30 min. After cooling, the solid formed was filtered off, dried and crystallized from ethanol.
In ethanol Reflux;
  • 43
  • C9H11NO2S2 [ No CAS ]
  • [ 33904-04-0 ]
YieldReaction ConditionsOperation in experiment
With dmap; di-<i>tert</i>-butyl dicarbonate In ethanol at -5 - 20℃; 4.2.3. General procedure for the synthesis of isothiocyanate derivatives 7a-7s General procedure: To a solution of primary amine compounds (1.0mmol) in absolute ethanol was added 10.0mmol CS2 and 10.0mmol triethyl amine. The mixture was stirred at room temperature until dithiocarbamate intermediate was formed. Then, the reaction was cooled in an ice bath at -5°C. 1.0mmol di-tert-butyl dicarbonate (Boc2O) and 3% mol of DMAP was dissolved in 0.5mL absolute ethanol, separately. At first, di-tert-butyl dicarbonate solution was added to the reaction mixture, and then the addition of DMAP solution was performed immediately. The reaction was kept in an ice bath for 5min and then was allowed to reach room temperature. The reaction was monitored by TLC. After 1-2h, the reaction mixture was concentrated under vacuo and 10mL water was added to residue. The mixture was extracted with chloroform (3×20mL) and organic phases were collected, dried over anhydrous Na2SO4 and concentrated under vacuum. The products were purified by preparative TLC.
  • 44
  • [ 33904-04-0 ]
  • [ 3616-44-2 ]
  • 1-(2,2-di(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In dichloromethane at 0 - 20℃; for 3h;
  • 45
  • [ 85630-20-2 ]
  • [ 33904-04-0 ]
  • O-4-chloro-2-((3,4-dimethoxyphenyl)carbamothioyl)phenylN,N-diethyl carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: O-(4-chloro)phenyl N,N-diethylcarbamate With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - -70℃; for 1.5h; Inert atmosphere; Stage #2: 4-isothiocyanato-1,2-dimethoxybenzene In tetrahydrofuran; cyclohexane at -70 - 20℃; for 17h; Inert atmosphere;
  • 46
  • [ 40400-15-5 ]
  • [ 33904-04-0 ]
  • 2-((3,4-dimethoxyphenyl)amino)benzo[b]thiophene-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 2-(2-iodophenyl)acetonitrile With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere; Stage #2: 4-isothiocyanato-1,2-dimethoxybenzene In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere;
  • 47
  • [ 33904-04-0 ]
  • [ 80-70-6 ]
  • C15H23N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate at 20℃; for 2h; Step 2 General procedure: Tothe stir solution of phenyl isothiocyanate derivative (1 eq.) in a minimum amount of ethyl acetate, add very slowly and dropwise1,1,3,3 tetramethylguanidine (1 eq.) at room temperaturefor 2 h. After completion of the reaction,the precipitate was filtered, the final product was dried and weighed.
  • 48
  • C15H25N2O2S2(1+) [ No CAS ]
  • [ 33904-04-0 ]
YieldReaction ConditionsOperation in experiment
With chloroformic acid ethyl ester; triethylamine In chloroform at 0 - 5℃; for 1.5h; Step 1: Synthesis of isothiocyanate General procedure: Asolution of aniline (1 eq.) and TEA (3.2 eq.) in THF was cooled to 0-5 °C withcontinuous stirring. To this cold reaction mixture, carbon disulfide (1.1 eq.) was added through the addition funnel. The reaction mixture wasallowed to stir for 6 h and monitored by TLC. The completion of the reaction(formation of salt) was checked by TLC in MeOH: Hexane: Ethyl acetate (1:6:3)mobile phase system. Dithiocarbamate salt was filtered off and dried. Then itwas dissolved in chloroform and TEA (1 eq.) and followed by ethyl chloroformate (1.1eq.) at 0-5 oCand allow to stir for 1.5 h then add 3M HCl solution and keep for 10 minsstirring. Then the organic layer wasseparated and dried over anhydrous sodium sulfateand concentrated under vacuum. It was purified by column chromatography usingsilica gel 60-120 mesh size as the stationaryphase.
  • 49
  • [ 3326-71-4 ]
  • [ 33904-04-0 ]
  • 1-[(furan-2-carbonyl)]-4-[3,4-(dimethoxy)phenyl]thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Reflux; General synthetic procedure for compounds 1-12 General procedure: 2-Furoic acid hydrazide (0.01 mol) and substituted phenylisothiocyanate(0.01 mol) were dissolved in methanol andthe mixture was refluxed overnight. After completion of thereaction, the mixture was left to cool down in order toprecipitate the solids. Finally, ethanol was used to purify theprecipitate [31].
  • 50
  • [ 557-68-6 ]
  • [ 33904-04-0 ]
  • 3,4-dimethoxy-N-[(2Z)-2-thietanylidene]aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With methyllithium lithium bromide In tetrahydrofuran; diethyl ether at -78℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
  • 51
  • [ 638-07-3 ]
  • [ 33904-04-0 ]
  • ethyl 2-((3,4-dimethoxyphenyl)amino)-4-oxo-4,5-dihydrothiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: ethyl (2-chloroaceto)acetate With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 0.5h; Stage #2: 4-isothiocyanato-1,2-dimethoxybenzene In 1,4-dioxane; mineral oil at 40℃; 4.1.1 General procedure 139 General procedure: The ethyl 4-chloroacetoacetate (5 mmol) was added to a solution of sodium hydride (60% in oil, 6 mmol) in 1,4-dioxane (4 mL) and stirred for 30 min at RT. To the reaction mixture was added a solution of aryl isothiocyanate (5 mmol) in 1,4-dioxane (1 mL) dropwise over 10 min. The temperature was allowed to reach 40°C. After 2 h at 40°C, the mixture was poured into H2O and the solid formed was collected, washed with H2O, and recrystallized from ethanol to give a desired product. All derivatives were synthesized with same method unless it is mentioned in detail.
33% Stage #1: ethyl (2-chloroaceto)acetate With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 0.5h; Stage #2: 4-isothiocyanato-1,2-dimethoxybenzene In 1,4-dioxane; mineral oil at 40℃; 4.1.1 General procedure 139 General procedure: The ethyl 4-chloroacetoacetate (5 mmol) was added to a solution of sodium hydride (60% in oil, 6 mmol) in 1,4-dioxane (4 mL) and stirred for 30 min at RT. To the reaction mixture was added a solution of aryl isothiocyanate (5 mmol) in 1,4-dioxane (1 mL) dropwise over 10 min. The temperature was allowed to reach 40°C. After 2 h at 40°C, the mixture was poured into H2O and the solid formed was collected, washed with H2O, and recrystallized from ethanol to give a desired product. All derivatives were synthesized with same method unless it is mentioned in detail.
  • 52
  • rac-cysteine [ No CAS ]
  • [ 33904-04-0 ]
  • C12H16N2O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In methanol; lithium hydroxide monohydrate at 20℃; for 24h; General procedure of compounds (1-17) General procedure: Various phenylisotiyocyanates (1 mmol) were added to the solution of L-cysteine (1 mmol) in methanol : water (1 : 1 v :v) at room temperature, and the mixture was stirred for 24 h. The precipitated solid was recrystallized from n-butanol and submitted for structural elucidation.
  • 53
  • [ 33904-04-0 ]
  • [ 476-28-8 ]
  • [ 2888543-32-4 ]
YieldReaction ConditionsOperation in experiment
39 % With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 16 Add lycorine (143mg, 0.5mmol), DMF (5mL), 3,4-dimethoxyphenyl isothiocyanate (244mg, 1.25mmol) successively to the reaction flask, add NaH (52mg , 1.3mmol), stirring at room temperature under the protection of argon. The reaction was detected by TLC until the raw materials disappeared, and the target compound was the main spot (developer: ethyl acetate, Rf=0.4), and about 15 mL of saturated NaHCO3 was added dropwise to the reaction solution in an ice bath, stirred at room temperature for a while and filtered, and the filter cake was washed with an appropriate amount of Washed with water, filtered and then stirred with a small amount of ethyl acetate, filtered to obtain a yellow solid (90 mg, yield 39%).
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[ 33904-04-0 ]

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