Chloroacetyl chloride → 2-Chloro-N-[2-(hydroxymethyl)phenyl]acetamide

HRID 1891349Notes

Reaction equation

HRID 1891349 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 214392-Aminobenzyl alcoholHCID 81531Diisopropylethylamine

Product 1

HCID 225912202-Chloro-N-[2-(hydroxymethyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To chloroacetyl chloride (3.0 mL, 37.7 mmol) in dry DCM (100 mL) was added 2-aminobenzyl alcohol (4.3 g, 34.9 mmol) followed by addition of diisopropylethylamine (13.0 mL, 78.6 mmol). The mixture was stirred at ambient temperature for 2 hrs. The mixture was quenched with saturated sodium bicarbonate. The organic layer was separated and washed with sat NaHCO3 (50 mL) and water (50 mL×2). The resulting solution was dried over MgSO4 and evaporated to afford 2-chloro-N-(2-hydroxymethyl-phenyl)acetamide as a brown oil in quantitative yield (7.0 g). MS: 182.0 (M−H2O)+; tR=1.46 min (method 1).

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. washwashed with sat NaHCO3 (50 mL) and water (50 mL×2)
  4. dry with materialThe resulting solution was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-12f62ad54bcf4559b0c3d58165c8883f
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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