Triethylamine → HCID 830996, compound

HRID 722707Notes

Reaction equation

HRID 722707 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:11]1([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:7]([C:6]1[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=1[NH:1][C:18](=[O:19])[CH:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 746372,2-Diphenylacetyl chlorideHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Product 1

HCID 830996HCID 830996, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-Amino-3-cyano-4,5-dimethylthiophene (152 mg; 1.0 mmol) and diphenylacetyl chloride (300 mg; 1.3 mmol) in dry methylene chloride (10 mL) under nitrogen at room temperature was added triethylamine (0.42 mL; 3.0 mmol) dropwise. After 1.5 h, the mixture was washed with 1N HCl. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was triturated with cold 30% ethylacetate/hexanes and filtered to give 162 mg (47%) of N-(3-Cyano-4,5-dimethyl-thiophen-2-yl)-2,2-diphenyl-acetamide as a white solid. ES-HRMS m/e calcd for C21H18N2OS (M+H+) 347.1213, found 347.1217.

Workup

  1. washthe mixture was washed with 1N HCl
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was triturated with cold 30% ethylacetate/hexanes
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e035e18472394a0cbcf2ea03b0c797f6
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Reaction notes

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