Triethylamine → Methyl 3-[(4-cyanobenzoyl)amino]thiophene-2-carboxylate

HRID 12144

Reaction equation

HRID 12144 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>ClCCl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[C:18]([O:20][CH3:21])=[O:19])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 2808363Methyl 3-[(4-cyanobenzoyl)amino]thiophene-2-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-cyanobenzoyl chloride (1.0500 g, 6.4 mmol), methyl 3-aminothiophenecarboxylate (1.0000 g, 6.4 mmol), and triethylamine (1 mL, 7.0 mmol) in dichloromethane was stirred at room temperature for 18 hours. The mixture was poured into a separatory funnel and washed by 1 N HCl. The organic layers were combined, dried over MgSO4, concentrated in vacuo, and chromatographed through a silica gel column to give the title compound 1.6588 g (91%). ES-MS 287 (M+1).

Workup

  1. additionThe mixture was poured into a separatory funnel
  2. washwashed by 1 N HCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customchromatographed through a silica gel column

Sources & evidence

ORD record
ord-81f661704e87442ca5d59fd306477d4f
Source dataset
uspto-grants-2010_06
Patent number
US07727982B2

Linked notes

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