Acetic Anhydride → N-(3-Iodo-2-methylphenyl)acetamide

HRID 2273611Notes

Reaction equation

HRID 2273611 reaction equation
[I:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(O)(=O)C>[C:10]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[C:3]=1[CH3:9])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 189261443-Iodo-2-methylaniline

Product 1

HCID 25138592N-(3-Iodo-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Charge a 5 L, 3 neck flask equipped with a mantle, stirrer, condenser, with 708 grams (5M) 3-Iodo-2-Methyl Aniline, followed by 700 ml glacial acetic acid. Add in a stream of 520 grams (5.1M) acetic anhydride and allow the solution to come to a gentle reflux for an hour. The solution is allowed to cool and poured in a stream in a large container of 8 L ice water. The product will crystallize immediately and is filtered and squeezed under vacuum and air-dried. Yield was 900 grams (Theoretical yield=918 g).

Workup

  1. additionCharge a 5 L, 3 neck flask
  2. customequipped with a mantle, stirrer, condenser
  3. temperaturea gentle reflux for an hour
  4. temperatureto cool
  5. customThe product will crystallize immediately
  6. filtrationis filtered
  7. customair-dried

Sources & evidence

ORD record
ord-bdaa9e2d9f2042d4b8974bc76fe0f94f
Source dataset
uspto-grants-2015_09
Patent number
US09125946B2

Reaction notes

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