Ammonia → 2-(4-Methoxyphenyl)acetamide

HRID 2176876Notes

Reaction equation

HRID 2176876 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-41bb5eaa0b9e40788f67484ffa0c3eae
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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