Ammonia → 2-(4-Methoxyphenyl)acetamide

HRID 1896240Notes

Reaction equation

HRID 1896240 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[NH3:17]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH2:17])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 76904-Methoxyphenylacetic AcidHCID 24386Thionyl Chloride

Product 1

HCID 2418682-(4-Methoxyphenyl)acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-methoxyphenyl)acetic acid (500 mg, 3.00 mmol) in DCM (30 ml) was added thionyl chloride (0.4 ml, 4.5 mmol) at 0° C. The reaction mixture was allowed to warm up to room temperature and continued to stirred overnight. Then aqueous ammonia (2 ml) was added to the reaction mixture. The white solid forming was filtered and dried under vacuum to obtained 350 mg (70%) of 2-(4-methoxyphenyl)acetamide as a white solid.

Workup

  1. customThe white solid forming
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5ad97b8f130c4fa1b36f0b06d47086ca
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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