Acetic Anhydride → N-(5-iodo-2-methylphenyl)acetamide

HRID 2373349Notes

Reaction equation

HRID 2373349 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH2:8])[CH:7]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH:8][C:10](=[O:12])[CH3:11])[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5228025-Iodo-o-toluidine

Product 1

HCID 14233595N-(5-iodo-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-iodo-2-methyl-phenylamine (20.4 g, 87.6 mmol) in 200 mL of dry CH2Cl2 was cooled to 0° C. and acetic anhydride (16.5 mL, 175 mmol) was added dropwise. The mixture was heated to 50° C. for 2 h and then cooled to 22° C. The resulting white precipitate was filtered to give c (18.4 g, 76%): MS m/z═276 (M+H).

Workup

  1. temperaturecooled to 22° C
  2. filtrationThe resulting white precipitate was filtered
  3. customto give c (18.4 g, 76%)

Sources & evidence

ORD record
ord-4931c974a94a4a97a4c5ef6253db6017
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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