Chloroacetyl chloride → 2-chloro-N-(4-iodophenyl)acetamide

HRID 1916649Notes

Reaction equation

HRID 1916649 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[I:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([I:6])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 108934-Iodoaniline

Product 1

HCID 7357922-chloro-N-(4-iodophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.0 mL (25.1 mmol) chloro-acetylchloride in 5 mL DCM are added to a solution of 5.00 g (22.83 mmol) 4-iodo-phenylamine and 7.0 mL (50.2 mmol) triethylamine in 100 mL DCM at 0° C. The ice bath is removed and the reaction is stirred for a further 1.5 h at RT. The reaction solution is diluted with 80 mL water and the organic phase is washed with saturated NaCl solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The residue is triturated with EtOAc, suction filtered and dried in the air.

Workup

  1. customThe ice bath is removed
  2. additionThe reaction solution is diluted with 80 mL water
  3. washthe organic phase is washed with saturated NaCl solution
  4. dry with materialThe organic phase is dried over MgSO4
  5. customThe residue is triturated with EtOAc, suction
  6. filtrationfiltered
  7. customdried in the air

Sources & evidence

ORD record
ord-d87c2720195a4776937624d9aa6b2843
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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