Chloroacetyl chloride → 2-Chloro-N-(2,6-diisopropylphenyl)acetamide

HRID 1666721Notes

Reaction equation

HRID 1666721 reaction equation
C(N(CC)CC)C.[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:12]=1[NH2:20])([CH3:10])[CH3:9].[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:21][CH2:22][C:23]([NH:20][C:12]1[C:11]([CH:8]([CH3:10])[CH3:9])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:17]([CH3:19])[CH3:18])=[O:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 32484Diisopropylaniline2×

Product 1

HCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

222 ml (1.59 mol) of triethylamine are added to a solution of 300 ml (1.59 mol) of 2,6-diisopropylphenylamine (starting product 1) in 11 of dichloromethane. The reaction mixture is cooled to 0° C. and then 127 ml (1.59 mol) of chloroacetyl chloride are added, drop by drop. Once the addition is finished, the ice bath is removed and the medium is stirred for 20 min. It is then poured into water and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated. The residue is filtered on a silica cake (eluent: dichloromethane). The filtrate is evaporated and then triturated in heptane. 345 g of 2-chloro-N-(2,6-diisopropylphenyl)acetamide are obtained in the form of a white solid. Yield=85%. M.p.=146-8° C.

Workup

  1. additionOnce the addition
  2. customthe ice bath is removed
  3. additionIt is then poured into water
  4. extractionextracted with dichloromethane
  5. customThe organic phases are collected
  6. washwashed with water
  7. dry with materialThey are dried over sodium sulfate
  8. customThe solvents are evaporated
  9. filtrationThe residue is filtered on a silica cake (eluent: dichloromethane)
  10. customThe filtrate is evaporated
  11. customtriturated in heptane

Sources & evidence

ORD record
ord-bcea093351154a4a970d78ec11e4589f
Source dataset
uspto-grants-2011_10
Patent number
US08044082B2

Reaction notes

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