Chloroacetyl chloride → HCID 14257921, compound

HRID 2231206Notes

Reaction equation

HRID 2231206 reaction equation
C(N(CC)CC)C.Cl.[C:9]1([CH:15]([NH2:25])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:26][CH2:27][C:28](Cl)=[O:29]>C(Cl)(Cl)Cl.C1CCCCC1>[Cl:26][CH2:27][C:28]([NH:25][CH:15]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)=[O:29]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2039693368770-54-7

Product 1

HCID 14257921HCID 14257921, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (254.9 g, 2.5 mol) was added with stirring to a solution of 1-phenyl-2-(3-methoxyphenyl)ethylamine hydrochloride (166.0 g, 0.63 mol) in chloroform (4 L) under nitrogen at 0° C. Then chloroacetyl chloride (142.2 g, 1.26 mol) was added dropwise over a period of 2 hrs. The resulting mixture was stirred at ambient temperature (about 25° C.) for 16 hrs, washed with 10% HCl (3×1 L) and water (1 L), and then the organic phase was dried over MgSO4. Evaporation of the solvent gave a dark oily residue which was dissolved in cyclohexane (2 L). Upon standing, the resulting solution gave solid crystals which were collected by filtration and dried to give 142.5 g of N-chloroacetyl-1-phenyl-2-(3-methoxyphenyl)ethylamine. A sample recrystallized twice from cyclohexane had a mp. 104°-105° C.

Workup

  1. washwashed with 10% HCl (3×1 L) and water (1 L)
  2. dry with materialthe organic phase was dried over MgSO4
  3. customEvaporation of the solvent
  4. customgave a dark oily residue which
  5. customthe resulting solution gave solid crystals which
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-11cf446c102d4d4bbf6446e0f995196d
Source dataset
uspto-grants-1988_11
Patent number
US04782058

Reaction notes

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