Acetic Anhydride → N-(2-Chloro-4-iodophenyl)acetamide

HRID 1936411Notes

Reaction equation

HRID 1936411 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11]>O1CCCC1>[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2829302-Chloro-4-iodoaniline

Product 1

HCID 18434368N-(2-Chloro-4-iodophenyl)acetamideYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloro-4-iodoaniline (25 g, 96.66 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C. and then treated with acetic anhydride (50.6 g, 500 mmol). The reaction mixture was stirred at 0° C. for 10 min and then allowed to warm to 25° C. where it was stirred for 15 h. The reaction mixture was then concentrated in vacuo to remove tetrahydrofuran. The residue was crystallized from ether (50 mL) and hexanes (50 mL). The solids were collected and washed with hexanes to afford N-(2-chloro-4-iodo-phenyl)-acetamide (23.87 g, 84%) as a white crystalline solid: EI-HRMS m/e calcd for C8H7ClINO (M+) 295.1526, found 295.1532.

Workup

  1. temperatureto warm to 25° C. where it
  2. stirringwas stirred for 15 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customto remove tetrahydrofuran
  5. customThe residue was crystallized from ether (50 mL) and hexanes (50 mL)
  6. customThe solids were collected
  7. washwashed with hexanes

Sources & evidence

ORD record
ord-119727781fd74d0c9d8e3c7675a05f0f
Source dataset
uspto-grants-2002_05
Patent number
US06388088B1

Reaction notes

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