Acetic Anhydride → N-(2-Chloro-4-iodophenyl)acetamide
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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-chloro-4-iodoaniline (25 g, 96.66 mm0l) 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 tetrahydrofaran. 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
- temperatureto warm to 25° C. where it
- stirringwas stirred for 15 h
- concentrationThe reaction mixture was then concentrated in vacuo
- customto remove tetrahydrofaran
- customThe residue was crystallized from ether (50 mL) and hexanes (50 mL)
- customThe solids were collected
- washwashed with hexanes
Sources & evidence
- ORD record
- ord-bdd30627578245bc831fcae01352c5db
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06369232B1
Reaction notes
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