Triethylamine → 2-bromo-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide

HRID 1772325Notes

Reaction equation

HRID 1772325 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8].C(N(CC)CC)C.[Br:25][C:26]([CH3:31])([CH3:30])[C:27](Br)=[O:28]>ClCCl>[Br:25][C:26]([CH3:31])([CH3:30])[C:27]([NH:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7](=[O:8])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromideHCID 719710(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone

Product 1

HCID 678141002-bromo-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottomed flask was charged with (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (2 g, 7.53 mmol) and a stirbar. Dichloromethane (75 mL, 0.1 M) was added, followed by triethylamine (1.573 ml, 11.29 mmol, 1.5 equiv). The solution was cooled to 0° C. for the addition of 2-bromo-2-methylpropanoyl bromide (1.163 ml, 9.41 mmol). The solution was stirred at room temperature 1 h, at which point LC/MS analysis showed complete conversion of the starting material. The solution was washed successively with water and brine before being dried with sodium sulfate and concentrated to give a quantitative yield of 2-bromo-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide as a yellow amorphous solid (m/z=414/416), which was used crude in the subsequent reaction.

Workup

  1. washThe solution was washed successively with water and brine
  2. dry with materialbefore being dried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e2ed6005010943dbb863defea4ee2ec9
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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