Chloroacetyl chloride → HCID 246995, compound

HRID 1014225Notes

Reaction equation

HRID 1014225 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C1COCC1>[Cl:19][CH2:20][C:21]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 83904-Methyl-3-nitroanilineHCID 8471Triethylamine

Product 1

HCID 246995HCID 246995, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methyl-3-nitroaniline (1.0 g, 6.58 mmol, Lancaster), triethylamine (2.00 g, 19.7 mmol, Aldrich), and chloroacetyl chloride (0.96 g, 8.55 mmol) in THF (50 mL) was stirred overnight at rt. The reaction was washed with 1M HCl (50 mL), concentrated by rotary evaporation, and placed under high vacuum to give 2-chloro-N-(4-methyl-3-nitrophenyl)acetamide (1.35 g, 90%). ESIMS (M+H)+=229.

Workup

  1. washThe reaction was washed with 1M HCl (50 mL)
  2. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-aea5b5ac0427433db5c7d298da7f3c6d
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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