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[ CAS No. 4074-74-2 ] {[proInfo.proName]}

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Chemical Structure| 4074-74-2
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Product Details of [ 4074-74-2 ]

CAS No. :4074-74-2 MDL No. :MFCD00613409
Formula : C9H10N2S Boiling Point : -
Linear Structure Formula :- InChI Key :RIHDPQKLSOXBOH-UHFFFAOYSA-N
M.W : 178.25 Pubchem ID :19995
Synonyms :

Calculated chemistry of [ 4074-74-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.83
TPSA : 44.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.36
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 2.67
Consensus Log Po/w : 2.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.205 mg/ml ; 0.00115 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.194 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.149 mg/ml ; 0.000836 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 4074-74-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4074-74-2 ]

* 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 [ 4074-74-2 ]

[ 4074-74-2 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 615-20-3 ]
  • [ 124-40-3 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
96% With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
80% Stage #1: dimethyl amine With copper(l) iodide for 0.5h; Stage #2: With potassium hydroxide In water for 1h; Stage #3: 2-chlorobenzo[d][1,3]thiazole With benzyl tri-n-butylammonium bromide In chloroform; water at 20℃; for 6h; chemoselective reaction;
78% In water at 20℃; for 5h; Green chemistry; General experimental procedure for the amination of 2-chlorobenzothiazole General procedure: The reaction was carried out in a 25 mL round bottom flask equipped with magnetic stir bar charged with 2-chlorobenzothiazole (1 mmol), aminating agent (2.0 equiv), and water (2 mL). The resulting reaction mixture was stirred at room temperature for 30 min to 5 h (varies with nature of the amine). The reaction progress was monitored by TLC. After the reaction, it was worked up with ethyl acetate. Crude product was purified by column chromatography (for piperazine derivatives column is not required). The identity and purity of the product was confirmed by 1H NMR, 13C NMR, and ESI-MS.
77% With potassium phosphate; (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; copper(II) acetate monohydrate In water at 30℃; for 22h; Schlenk technique; Inert atmosphere;
In ethanol Heating;
In water at 25 - 30℃; for 24h;
In water at 160℃; for 15h; Yield given;

  • 2
  • [ 615-20-3 ]
  • [ 33513-42-7 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
90% With 5 wt% ruthenium/carbon; lithium tert-butoxide at 80℃; for 8h;
86% With ammonia In water at 240℃; for 0.5h;
at 150 - 160℃; for 5h;
  • 3
  • [ 52260-27-2 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
With COCl2 In 1,4-dioxane at 70℃;
  • 4
  • [ 705-62-4 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride at 50 - 55℃; for 4h;
82% With pyridine; [bis(acetoxy)iodo]benzene; nickel dibromide In 1,4-dioxane at 25℃; for 0.166667h;
With lead(II) dihydrogen orthophosphate; H2<Pb(H2PO4)2(HPO4)2>; buffer solution In methanol for 1.5h; Heating;
  • 5
  • [ 103-83-3 ]
  • [ 615-20-3 ]
  • [ 4074-74-2 ]
  • N-benzyl-N-methylbenzo[d]thiazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 2% 2: 98% In tetrahydrofuran at 100℃; for 96h;
  • 6
  • [ 680-31-9 ]
  • [ 615-20-3 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
64% at 150℃; for 15h;
  • 7
  • [ 615-20-3 ]
  • [ 598-56-1 ]
  • [ 4074-74-2 ]
  • [ 108656-84-4 ]
YieldReaction ConditionsOperation in experiment
1: 94% 2: 5.5% In tetrahydrofuran at 100℃; for 96h;
  • 8
  • [ 615-20-3 ]
  • [ 996-35-0 ]
  • [ 4074-74-2 ]
  • [ 136540-11-9 ]
YieldReaction ConditionsOperation in experiment
1: 79% 2: 20% In tetrahydrofuran at 100℃; for 96h;
  • 9
  • [ 615-20-3 ]
  • [ 7378-99-6 ]
  • [ 4074-74-2 ]
  • [ 136540-10-8 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 97% In tetrahydrofuran at 100℃; for 96h;
  • 10
  • [ 615-20-3 ]
  • [ 98-94-2 ]
  • [ 4074-74-2 ]
  • [ 136540-12-0 ]
YieldReaction ConditionsOperation in experiment
1: 4% 2: 94% In tetrahydrofuran at 100℃; for 96h;
  • 11
  • [ 4074-74-2 ]
  • [ 36016-40-7 ]
  • 3-Amino-2-(dimethylamino)benzothiazol-3-ium-(mesitylen-2-sulfonat) [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% In tetrahydrofuran at 4℃; for 63h;
  • 12
  • [ 2782-91-4 ]
  • [ 615-43-0 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
81% In N,N-dimethyl-formamide at 100℃; for 20h;
  • 13
  • [ 13829-06-6 ]
  • [ 137-07-5 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: N,N,N',N'-tetramethylchlorformamidinium chloride; 2-amino-benzenethiol With triethylamine In chloroform at -30 - -20℃; Stage #2: With silica gel In chloroform at 20℃; for 4.5h;
  • 14
  • 3-(2-bromophenyl)-1,1-dimethyl-thiourea [ No CAS ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
97% With caesium carbonate In 1,4-dioxane at 80℃; for 1h;
  • 15
  • N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate [ No CAS ]
  • [ 137-07-5 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine In N,N-dimethyl-formamide for 24h; Heating;
  • 16
  • [ 13037-60-0 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / Cs2CO3 / n-BuPAd2; Pd2dba3 / dioxane / 1 h / 80 °C
  • 17
  • [ 4074-74-2 ]
  • [ 107550-91-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / tetrahydrofuran / 63 h / 4 °C 2: 10 percent / Et(i-Pr)2N / 1,2-dichloro-ethane / 0.33 h / Heating
  • 18
  • [ 137-26-8 ]
  • [ 1205678-85-8 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
70% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 19
  • [ 137-26-8 ]
  • [ 614-76-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
69% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 20
  • [ 137-26-8 ]
  • [ 615-43-0 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
36% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 21
  • [ 137-26-8 ]
  • [ 10113-39-0 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
71% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 22
  • [ 137-26-8 ]
  • [ 19591-17-4 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
83% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; for 24h;
  • 23
  • [ 137-26-8 ]
  • [ 61613-20-5 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
48% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 24
  • [ 137-26-8 ]
  • [ 15310-02-8 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
50% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 25
  • [ 137-26-8 ]
  • [ 143321-89-5 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
70% With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;
  • 26
  • [ 95-16-9 ]
  • [ 33513-42-7 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
86% With silver(I) acetate; sodium t-butanolate In neat (no solvent) at 120℃; for 5h; Inert atmosphere;
51% With p-Toluic acid; silver carbonate at 130℃; for 12h; regioselective reaction;
47% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; acetic acid In water; 1,2-dichloro-ethane at 90℃; for 12h; Green chemistry; General experimental procedure Benzoxazole (1.0 mmol), N,N-disubstituted formamide (15 mmol), TBAI (0.2 equiv/74 mg), TBHP (70% aqueous solution, 10 mmol/1.37 mL), and acetic acid (5.0 equiv) in 1,2-dichloroethane (3.0 mL) were added to a reaction vessel in air. The reaction mixture was heated in an oil bath at 90 °C for 12 h. After completion of the reaction, the mixture was quenched by addition of a saturated solution of sodium disulfite (4.0 mL, for removal of excess TBHP) and a saturated solution of sodium hydrogen carbonate (4.0 mL). Then the mixture was extracted with ethyl acetate (3 × 15 mL), combined organic phases were dried over anhydrous Na2SO4 and the organic solvent was removed under vacuum. The crude residue was purified by chromatography on a silica gel column affording the desired product.
With p-Toluic acid; silver carbonate at 130℃; for 12h; Sealed tube;

  • 27
  • [ 2516-40-7 ]
  • [ 68-12-2 ]
  • [ 4074-74-2 ]
  • 28
  • [ 4314-19-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.2 h / 20 °C / Inert atmosphere 2: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / toluene / 0.23 h / 110 °C / Inert atmosphere
  • 29
  • [ 405136-89-2 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
92% With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 110℃; for 0.233333h; Inert atmosphere;
  • 30
  • [ 95-16-9 ]
  • CuCl2*2C2H7N*2ClH [ No CAS ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetonitrile at 30℃; for 5h;
  • 31
  • [ 124-40-3 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
91% With 5 wt% ruthenium/carbon; lithium tert-butoxide at 80℃; for 8h;
  • 32
  • [ 615-20-3 ]
  • [ 1467-79-4 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
90% With 5 wt% ruthenium/carbon; lithium tert-butoxide at 80℃; for 8h;
  • 33
  • [ 615-20-3 ]
  • [ 4637-24-5 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
76% With 5 wt% ruthenium/carbon; lithium tert-butoxide at 80℃; for 8h;
  • 34
  • [ 615-20-3 ]
  • [ 1188-33-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
72% With 5 wt% ruthenium/carbon; lithium tert-butoxide at 80℃; for 8h;
  • 35
  • [ 615-20-3 ]
  • [ 18503-89-4 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
69% With 5 wt% ruthenium/carbon; lithium tert-butoxide at 80℃; for 8h;
  • 36
  • [ 136-95-8 ]
  • [ 64-18-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
93% With tris(pentafluorophenyl)borate; phenylsilane In dibutyl ether at 100℃; Schlenk technique; Inert atmosphere;
  • 37
  • [ 4074-74-2 ]
  • [ 108-24-7 ]
  • [ 118215-03-5 ]
YieldReaction ConditionsOperation in experiment
59% With oxygen; copper diacetate at 85℃; for 36h; Schlenk technique; Sealed tube;
  • 38
  • [ 103-72-0 ]
  • [ 33513-42-7 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
42% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane at 90℃; for 48h;
  • 39
  • [ 62-53-3 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere 2: tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide / decane / 48 h / 90 °C
  • 40
  • [ 615-43-0 ]
  • [ 16420-13-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine; copper(l) iodide; 8-quinolinol; sulfur; potassium hydroxide at 80℃; for 0.5h; Microwave irradiation; 1 Example 1: N,N-Dimethyl-2-benzothiazolamine Add 2 mmol of 2-iodoaniline, 2.5 mmol of sulfur powder, 1 mmol of N,N-dimethylaminothioformoyl chloride to the reaction vessel, and sequentially add 0.1 mmol of cuprous iodide, 8-hydroxyquinoline.0.1 mmol, potassium hydroxide 3 mmol, pyridine 3 mL. Placed in a microwave reactor at a power of 150 W and heated to 80 °C for 30 min. After the reaction was completed, it was cooled to room temperature and concentrated under reduced pressure. The product was purified by column chromatography to give a yellow solid with a yield of 90%.
83% With potassium <i>tert</i>-butylate; copper(I) bromide In tetrahydrofuran at 60℃; for 4h; Schlenk technique; General procedure for synthesis of 2-aminobenzothiazoles derivatives (3a-i) A mixture of 2-iodoanilines (1.0 mmol), THF (3 mL), and t-BuOK (3 mmol) was stirred in a 10-mL sealed Schlenk tube for 5 min, and then dimethylthiocarbamoyl chloride (1.2 mmol) and CuBr (10 mol %) were added. The reaction mixture was heated at 60 °C until completion as indicated by TLC. Then the mixture was cooled down to room temperature and quenched with sat. NH4Cl solution (5 mL). The aqueous phase was extracted with EtOAc (3 x10 mL). The combined organic phases were dried (Na2SO4), and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography. N,N-Dimethybenzo[d]thiazol-2-amine (3a) Brown solid; m.p.: 83-85 °C; 1H NMR (400 MHz, CDCl3): δ 7.57 (d, J 8 Hz, 2H), 7.28 (t, J 8.0 Hz, 1H), 7.05 (t, J 7.8 Hz, 1H), 3.21 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 168.3, 152.7, 130.4, 125.7, 120.7, 120.4, 118.5, 39.8; HRMS (ESI): calcd for C9H10N2S: 178.0565; found: 178.0557.
  • 41
  • [ 16420-13-6 ]
  • [ 615-36-1 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
84% With potassium <i>tert</i>-butylate; copper(I) bromide In tetrahydrofuran at 60℃; for 4h; Schlenk technique; General procedure for synthesis of 2-aminobenzothiazoles derivatives (3a-i) General procedure: A mixture of 2-iodoanilines (1.0 mmol), THF (3 mL), and t-BuOK (3 mmol) was stirred in a 10-mL sealed Schlenk tube for 5 min, and then dimethylthiocarbamoyl chloride (1.2 mmol) and CuBr (10 mol %) were added. The reaction mixture was heated at 60 °C until completion as indicated by TLC. Then the mixture was cooled down to room temperature and quenched with sat. NH4Cl solution (5 mL). The aqueous phase was extracted with EtOAc (3 x10 mL). The combined organic phases were dried (Na2SO4), and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography.
  • 42
  • [ 16906-70-0 ]
  • [ 95-51-2 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); potassium <i>tert</i>-butylate In dimethyl sulfoxide at 100℃; 4.3. Typical procedure for the preparation of 2-aminobenzothiazoles starting from2-chloroanilines in the presence of Pd(PPh3)4 and KOt-Bu (TP3) A dried tube, equipped with a magnetic stirred and a septum, 2-chloroaniline (0.13 g,1.0mmol) was dissolved in DMSO (3mL), and KOt-Bu (0.34 g, 3mmol) was added. Themixture was stirred for 5min, and then dithiocarbamate (0.30 g, 1.5mmol) and tetrakispalladium(57.7mg, 5 mmol%) were added. The reaction mixture was then heated at100°C and checked by TLC until the starting material was finished. The reaction wascooled down to room temperature, and then quenched with sat. NH4Cl solution (5mL)and extracted with ethyl acetate, dried over anhydrous Na2SO4 and concentrated undervacuum. The residue was purified by flash column chromatography to afford the desiredproduct (153mg, 86%).
82% With tetrakis(triphenylphosphine) palladium(0); potassium <i>tert</i>-butylate In dimethyl sulfoxide at 100℃; Preparation of 2-Aminobenzothiazoles with Potassium tert-Butoxideand Tetrakis(triphenylphosphine)palladium; Typical Procedure General procedure: In a dried tube, equipped with a magnetic stirrer and a septum, 2-chloroaniline (1.0 mmol) was dissolved in DMSO (3 mL), and t-BuOK(3.0 mmol) was added. The mixture was stirred for 5 min, then dithiocarbamate(1.5 mmol) and tetrakis(triphenylphosphine) palladium(5 mol %) were added. The reaction mixture was heated at 100 °C andthe progress of the reaction was checked by TLC until the starting materialwas consumed. The mixture was cooled to r.t., and the reactionwas quenched with sat. NH4Cl solution (5 mL). The mixture was extractedwith EtOAc, dried over anhydrous Na2SO4 and evaporated undervacuum. The residue was purified by flash column chromatographyto afford the desired product.N,N-Dimethylbenzo[d]thiazol-2-amine (3a)According to the typical procedure, the residue was purified by flashchromatography on silica gel (petroleum ether/EtOAc, 3:1) to give thetarget compound.Yield: 146 mg (82%); brown solid; mp 83-85 °C.1H NMR (400 MHz, CDCl3): δ = 7.57 (d, J = 7.6 Hz, 2 H), 7.28 (t, J =8.0 Hz, 1 H), 7.09 (t, J = 6.8 Hz, 1 H), 3.21 (s, 6 H).13C NMR (100 MHz, CDCl3): δ = 168.32, 152.68, 130.44, 125.72,120.72, 120.40, 118.50, 39.77.HRMS (ESI): m/z calcd for C9H10N2S: 178.0565; found: 178.0572
  • 43
  • [ 103-72-0 ]
  • [ 124-40-3 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
75% With water In acetonitrile at 70℃; for 4h; Electrochemical reaction; Inert atmosphere; Green chemistry;
  • 44
  • [ 137-07-5 ]
  • [ 16420-13-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate; copper dichloride In tetrahydrofuran at 60℃; for 2.5h; Typical procedure for the preparation of 2-aminobenzoxazoles in the presence of K2CO3/CuCl2 (TP) General procedure: To a dried tube equipped with a magnetic stirrer and a septum, 2-aminophenol (1.0 mmol) was dissolved in THF (2.5 mL), and K2CO3 (1.0 mmol) was added. The mixture was stirred for 5 minutes, thiocarbamoyl chloride (3.0 mmol) and copper chloride (5 mol %) were added. The reaction mixture was then heated at 60 °C and checked by TLC until the starting material was finished. The reaction was cooled down to room temperature, quenched with sat. NH4Cl solution (5 mL) and extracted with ethyl acetate, dried over anhydrous Na2SO4 and then evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product.
  • 45
  • [ 95-51-2 ]
  • [ 16420-13-6 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
91% With potassium <i>tert</i>-butylate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; Typical procedure for the preparation of 2-aminobenzothiazoles in the presence of potassium tert-butoxideand Bis(dibenzylideneacetone) palladium (TP ) General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 °C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product.
  • 46
  • [ 615-43-0 ]
  • [ 16906-70-0 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
82% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 100℃; for 4.5h; 4.1. Typical procedure for the preparation of 2-aminobenzothiazoles starting from2-iodoanilines in the presence of KOt-Bu (TP1) Using a dried tube, equipped with a magnetic stirrer and a septum, 2-iodoaniline (0.22 g,1.0mmol) was dissolved in DMSO (3mL), and KOt-Bu (0.34 g, 3mmol) was added. Themixture was stirred for 5min, then dithiocarbamate (0.296 g, 1.5mmol) was added. Thereaction mixture was heated at 100°C and checked by TLC until the starting material wasfinished. The reaction mixture was cooled down to room temperature and then quenchedwith sat. NH4Cl solution (5mL) and extracted with ethyl acetate (10mL×3), dried overanhydrous Na2SO4 and concentrated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product (146mg, 82%).
  • 47
  • [ 16906-70-0 ]
  • [ 615-36-1 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
81% With potassium <i>tert</i>-butylate; copper(II) oxide In dimethyl sulfoxide at 100℃; 4.2. Typical procedure for the preparation of 2-aminobenzothiazoles starting from2-bromoanilines in the presence of CuO and KOt-Bu (TP2) A dried tube, equipped with a magnetic stirred and a septum, 2-bromoaniline (0.17 g,1.0mmol) was dissolved in DMSO (3mL), KOt-Bu (0.34 g, 3mmol) was added. The mixturewas stirred for 5 min, and then dithiocarbamate (0.296 g, 1.5mmol) and copper oxide(6.4mg, 8 mmol%) were added. The reaction mixture was heated at 100°C and checkedby TLC until the starting material was finished. The reaction mixture was cooled downto room temperature, and then quenched with sat. NH4Cl solution (5mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by flash column chromatography to afford the desired product(144mg, 81%).
  • 48
  • [ 95-16-9 ]
  • [ 124-40-3 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
89% With silver(I) acetate; sodium t-butanolate In neat (no solvent) at 120℃; for 5h; Inert atmosphere;
  • 49
  • [ 615-43-0 ]
  • [ 128-04-1 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
83% With copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h; Sealed tube;
  • 50
  • [ 16954-69-1 ]
  • [ 124-38-9 ]
  • [ 4074-74-2 ]
YieldReaction ConditionsOperation in experiment
67% With 2-Amino-6-methylpyridine; trimethylamine-borane In 1,2-dichloro-ethane at 100℃; for 6h; Schlenk technique; chemoselective reaction;
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