Chloroacetyl chloride → HCID 4425116, compound

HRID 359062Notes

Reaction equation

HRID 359062 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:18](=[O:19])[CH2:17][Cl:16])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 773174-Pyridinemethanamine

Product 1

HCID 4425116HCID 4425116, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

The starting material was obtained as follows: A solution of 4-pyridylmethylamine (1.08 g) and triethylamine (1.0 g) in dichloromethane (25 ml) was added slowly over 30 minutes to a chilled, stirred solution of chloroacetyl chloride (1.2 g) in dichloromethane (7.5 ml). The reaction mixture was maintained at 0-5° C. throughout the addition, stirred for a further 30 minutes and allowed to warm to room temperature. The reaction mixture was washed with water (2×10 ml) and dried over MgSO4. Evaporation of the solvent under reduced pressure gave N-(4-pyridylmethyl)chloroacetamide as a brown oil, which was used immediately.

Workup

  1. customThe starting material was obtained
  2. temperatureto warm to room temperature
  3. washThe reaction mixture was washed with water (2×10 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0f0fdd74f22d4825b988f7fd1b8feb19
Source dataset
uspto-grants-1991_03
Patent number
US04999377

Reaction notes

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