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[ CAS No. 942-06-3 ]

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2D
Chemical Structure| 942-06-3
Chemical Structure| 942-06-3
Structure of 942-06-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 942-06-3 ]

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Related Doc. of [ 942-06-3 ]

SDS

Product Details of [ 942-06-3 ]

CAS No. :942-06-3MDL No. :MFCD00075034
Formula :C8H2Cl2O3Boiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :217.01Pubchem ID :70334
Synonyms :

Computed Properties of [ 942-06-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 942-06-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 942-06-3 ]

  • Downstream synthetic route of [ 942-06-3 ]

[ 942-06-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 942-06-3 ]
  • [ 109292-68-4 ]
  • C26H33Cl2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With sulfuric acid; In toluene; at 120℃; for 5h; 3-(dihexylamino)phenol (Compound F-8, 3.62 mmol) and [942-06-3]4,5-dichlorophthalic anhydride(Compound G-9, 5.43 mmol, purchased from Tokyo Chemical Industry Co., Ltd., and vendor code D2335) is dissolved in toluene (10 mL),Stir at 120 C. for 5 hours.After cooling to room temperature, the solvent was distilled off under reduced pressure to obtain a reddish purple oily compound.The residue was purified by silica gel column chromatography to obtain compound D-9. The yield was 91%. The reaction formula is shown below.
  • 2
  • [ 51-67-2 ]
  • [ 942-06-3 ]
  • 4,5-dichloro-N-(4-hydroxyphenethyl)phthalimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With acetic acid; for 1.5h;Reflux; General procedure: A mixture of tyramine 8 (274 mg, 2.0 mmol) and the correspondinganhydride (1.9 mmol) in glacial acetic acid (3 mL) were refluxed for 1.5 h. After cooling of the reactionmixture to ambient temperature, cold H2O (10 mL) was added and the resultant precipitate wasfiltered, washed several times with cold water, and dried under reduced pressure (7a, 7e). When theproduct did not precipitate from the solution (7b?d, 7h?j), H2O (15 mL) was added, and the aqueousphase was extracted several times with EtOAc. The combined organic layers were washed with 1 MNaHCO3, dried over Na2SO4, and concentrated in vacuo to yield the crude products, which were usedwithout further purification.
  • 3
  • [ 942-06-3 ]
  • [ 1694-31-1 ]
  • [ 93296-41-4 ]
YieldReaction ConditionsOperation in experiment
56% 5,6-Dichloroindan-l,3-dione was synthesized according to (Buckle et al., 1973). 4,5- Dichlorophthalic anhydride (2.0 g, 9.2 mmol) was added to Ac20 (4.7 mL, 5.0 g, 50 mmol), Et3N (2.6 mL) was added to this suspension and the obtained mixture was treated with tert- butyl acetoacetate (1.5 mL, 1.5 g, 9.2 mmol). The reaction mixture was stirred at r. t. for 18 h, then ice (3 g) and concentrated HCl (3 mL, 37percent) were added. Then one more portion of HCl was added (13 mL, 5 M) and the dark solution was stirred at 75-80 °C for 1 h. The reaction mixture was allowed to cool down to r. t. and extracted with CH2CI2 (3 times). The combined organic phases were dried over Na2S04, filtered and concentrated under reduced pressure. Recrystallization from hexane : EtOAc 1 : 1 yielded 1.1 g (56percent) of the product. - 1H NMR (400 MHz, DMSO-d6): 8.17 (s, 2 H), 3.39 (s, 2 H). - 13C NMR (100 MHz, DMSO-d6): 196.43, 142.85, 139.07, 125.21, 45.77.
  • 4
  • [ 942-06-3 ]
  • C11H17NO2*ClH [ No CAS ]
  • [ 1425092-74-5 ]
YieldReaction ConditionsOperation in experiment
76% In acetic acid; at 100℃; for 2h; Compound 2 (0.2 g, 1 mmol) and 3 (0.2 g, 1 mmol) was dissolved in acetic acid (10 mL), stirred at 100° C. for 2 h. The mixture was cooled to rt and quenched by water (10 mL), extracted by EtOAc (3×20 mL), dried, concentrated to give the title compound 4 (0.3 g, 76percent).
  • 5
  • [ 942-06-3 ]
  • [ 24544-04-5 ]
  • C20H19Cl2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With acetic acid; at 120℃; for 8h; From the commercialized compound [942-06-3]4,5-dichlorophthalic anhydride (430 mg, 2 mmol, 1 eq) and containing 2,6-diisopropylaniline(387 mg, 2.2 mmol, 1.1 eq) in glacial acetic acid (10 mL), the reaction temperature was raised to 120 ° C, refluxed for approximately 8 h,The color change of the reaction solution was observed, the degree of the reaction was checked by TLC, and the reaction solution was spin-dried and then subjected to column chromatographyTo obtain the compound 1a, melting point: 180 ° C, yield 98percent.
  • 6
  • [ 942-06-3 ]
  • [ 150-30-1 ]
  • 2-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid; for 6h;Reflux; A solution of [942-06-3]4,5-dichlorophthalic anhydride (5 mmol) and phenylalanine (5 mmol) in glacialacetic acid (7 mL) was stirred and heated under reflux for 6 h. The product of this reaction (Figure 4a,yield 85percent) was precipitated by addition of cold water, filtered and dried to afford grams and percent yieldof 2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)-3-phenylpropanoic acid (NS-1502). 1H-NMR (400 MHz,DMSO-d6): delta 8.16 (2H, s, H-3,4), 7.15 (5H, m, H-20-24), 5.11 (1H, dd, J = 11.53, 4.82 Hz, H-13), 3.48(1H, dd, J = 14.20, 4.82 Hz, H-15a), 3.30 (1H, dd, J = 14.20, 11.53 Hz, H-15a); 13C-NMR (100 MHz,DMSO-d6): delta 33.85 (C-15), 53.41 (C-13), 125.68 (C-3,4), 126.59 (C-24), 128.32 (C-20,21), 128.66 (C-22,23),130.33 (C-5,6), 137.11 (C-19), 138.06 (C-1,2), 165.17 (C-7,9), 169.64 (C-12); HRESIMS: 385.99630 m/z[C17H11Cl2NO4 + Na]+ (Calcd. 385.99573).
  • 7
  • [ 942-06-3 ]
  • [ 108-91-8 ]
  • 5,6-dichloro-2-cyclohexyl-isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With propionic acid; at 140℃; for 3h;Inert atmosphere; In the one-port flask was added 100ml of 4,5-dichloro phthalic anhydride (0.78g, 3.6mmol), cyclohexylamine, or n-butylamine (5.4mmol), 10ml propionic acid, under nitrogen, 140 heating reflux 3h. Propionic acid was distilled off under reduced pressure, column chromatography to obtain the product.5,6-dichloro-2-cyclohexyl-isoindole-1,3-dione (141a), yield 90percent.
  • 8
  • [ 942-06-3 ]
  • C11H17NO2*(x)ClH [ No CAS ]
  • [ 1425092-74-5 ]
YieldReaction ConditionsOperation in experiment
76% With acetic acid; at 100℃; for 2h; Step2: Compound 2 (0.2 g, 1 mmol) and 3 (0.2 g, 1 mmol) was dissolved in acetic acid ( 10 mL), stirred at 100 °C for 2 h. The mixture was cooled to rt and quenched by water (10 mL), extracted by EtOAc (3 x 20 mL), dried, concentrated to give the title compound 4 (0.3 g, 76percent).
  • 9
  • [ 942-06-3 ]
  • [ 27527-05-5 ]
  • [ 1416811-70-5 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In toluene;Reflux; Dean-Stark; A suspension of (2S)-2-amino-3-cyclohexylpropanoic acid (3.16 g, 18.43 mmol), triethylamine (7.67 mL, 55.30 mmol) and [942-06-3]4,5-dichlorophthalic anhydride (4.0 g, 18.43 mmol) in toluene (30 mL) was refluxed overnight under Dean?Stark conditions. The reaction solvent was evaporated and then purified by column chromatography to give   (S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid as a white solid (6.28 g, 92percent). 1H NMR (400 MHz, DMSO-d6) delta 13.19 (br s, 1H), 8.18 (s, 2H), 4.82?4.78 (m, 1H), 2.13?2.05 (m, 1H), 1.92?1.84 (m, 1H), 1.78?1.76 (m, 1H), 1.59?1.50 (m, 4H), 1.15?1.02 (m, 4H), 0.95?0.81 (m, 2H); LC?MS (ESI) m/z 368 [M ? H]?.
  • 10
  • [ 942-06-3 ]
  • [ 1160297-82-4 ]
  • [ 1160297-71-1 ]
YieldReaction ConditionsOperation in experiment
42% Example 2: Synthesis of PPAT Inhibitor Compound 6A mixture of amine bis-hydrochloride 1 (502 mg, 2.22 mM), anhydrous sodium acetate (240 mg, 2.92 mM) and aldehyde 2 (398 mg, 2.27 mM) in pyridine (20 mL) was heated to reflux under N2 for 16 hours. The mixture was cooled to room temperature and most of the pyridine was removed in vacuo. The residue was treated with CH2Cl2 (100 mL) and saturated NaHCO3 aqueous solution (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (1 X 100 mL, 2 X 30 mL). The combined organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate- ethyl acetate/methanol 95: 5) to give 3 as a off-white waxy solid (386 mg, 56 percent). (NMR of parent compound: 1HNMR 2.58(2H, CH2-CH2NH), 2.82(2H, CH2-CH2-NH), 5.3O(1H, ArCH-NH), 6.92(1H, 6-phenyl proton), 7.22(1 H, 5-phenyl proton), 7.42 (1 H, imidazole proton), 7.55 (1 H, 5-phenyl proton)). A solution of compound 3 (150 mg, 0.48 mM) and anhydride 4 (111 mg, 0.48 mM) in DMSO (10 mL) was heated at 65°C (bath temperature) under N2 for 16 hours. The mixture was allowed to cool to room temperature and was treated with 300 mL (ether/ethylacetate: 1/1). This was washed with brine (2 X 50 mL) followed by water (3 X 50 mL) and then dried (Na2SO4). The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (ethyl acetate/ hexane: 4/2 to 1/0) to give compound 5. This was recrystallized from chloroform/hexane and dried in vacuum oven at 65°C overnight to give 5 as white powder (108 mg, 42 percent). 1H NMR (dmso-d): was not well defined due to rotomers. MS: m+1 = 526 and m-1 = 524.
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