Chloroacetyl chloride → 2-Chloro-N-(5-chloro-2-hydroxyphenyl)acetamide

HRID 1750143Notes

Reaction equation

HRID 1750143 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl:10][CH2:11][C:12](Cl)=[O:13]>C(Cl)Cl.N1C=CC=CC=1>[Cl:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9])=[O:13]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 72652-Amino-4-chlorophenol

Product 1

HCID 74542742-Chloro-N-(5-chloro-2-hydroxyphenyl)acetamideYield 55%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 2-amino-4-chlorophenol (30 g, 209 mmol) in DCM (200 mL) and pyridine (17 mL) was added a solution of chloroacetyl chloride in DCM (23.6 g, 230 mmol in 75 mL). The mixture was allowed to reach rt slowly and was subsequently stirred for 18 h. The precipitate was filtered, washed with DCM, and dried overnight at 50° C. to give crude 2-chloro-N-(5-chloro-2-hydroxyphenyl)acetamide (intermediate 56) (26 g, 55%), as a brown solid which was used in the next step without any further purification.

Workup

  1. customto reach rt
  2. filtrationThe precipitate was filtered
  3. washwashed with DCM
  4. customdried overnight at 50° C.

Sources & evidence

ORD record
ord-3c91bc869c2b4b2fa6983f505711757f
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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