4-Chlorobenzoyl chloride → HCID 20775759, compound

HRID 1015616Notes

Reaction equation

HRID 1015616 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:18]([Cl:17])=[CH:19][CH:20]=1)=[O:4]

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 20775759HCID 20775759, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To mixture of methyl-3-amino-5-phenylthiophene-2-carboxylate (100 mg, 0.428 mmol) in anhydrous pyridine (4.3 ml) was added p-chlorobenzoyl chloride (71 μl, 0.556 mmol). The mixture was stirred for 3 hours at room temperature and concentrated. Purification chromatography (silica gel, hexane to hexane:ethyl acetate; 95:5) gave 145 mg (91% yield) of 3-(4-Chloro-benzoylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester. 1H NMR (CDC3, 400 MHz) 8.54 (s, 1H), 7.99-7.96 (m, 2H), 7.73-7.71 (m, 2H); 7.52-7.50 (m, 2H), 7.46-7.39 (m, 3H), 3.95 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customPurification chromatography (silica gel, hexane to hexane:ethyl acetate; 95:5)

Sources & evidence

ORD record
ord-d090cd4b49b94fa597d68251a5bacae7
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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