Triethylamine → HCID 53876345, compound

HRID 395740Notes

Reaction equation

HRID 395740 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6]([NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7])#[N:2].C(N(CC)CC)C.[Cl:26][C:27]1[C:28]2[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=2[S:30][C:31]=1[C:32](Cl)=[O:33]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6]([NH:8][C:9]1[C:10]([NH:15][C:32]([C:31]2[S:30][C:29]3[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=3[C:27]=2[Cl:26])=[O:33])=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 10705025HCID 10705025, compound

Product 1

HCID 53876345HCID 53876345, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N1-(3-cyanobenzoyl)-1,2-benzenediamine (500 mg, 2.1 mmol) and triethylamine (0.44 mL, 3.2 mmol) in methylene chloride (100 mL) was added 3-chlorobenzo[b]thiophene-2-carbonyl chloride (490 mg, 2.1 mmol). After stirring for 20 h, the mixture was concentrated in vacuo and chromatographed (silica gel, 25% ethyl acetate/75% hexane) to give 660 mg (73%) of the title compound as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customchromatographed (silica gel, 25% ethyl acetate/75% hexane)

Sources & evidence

ORD record
ord-b179603084844df1affc2c395ba23724
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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