Chloroacetyl chloride → HCID 12846074, compound

HRID 463348Notes

Reaction equation

HRID 463348 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)(Cl)Cl>[Cl:24][CH2:25][C:26]([NH:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]([OH:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 222432-Amino-1,2-diphenylethanol

Product 1

HCID 12846074HCID 12846074, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2-hydroxy-1,2-diphenylethylamine (95.5 g, 0.39 m) (obtained by catalytic reduction of benzoin oxime) and triethylamine (43.3 g, 0.429 m) in chloroform (1 liter) maintained under nitrogen was added dropwise chloroacetylchloride (46.2 g, 0.41 m) and the mixture heated to reflux for 1 hour. After cooling, the mixture was washed with 10% HCl (1 liter) and water and the organic phase dried over MgSO4. The solvent was evaporated to a solid residue which was recrystallized from methanol to give 91.0 g of N-chloroacetyl-2-hydroxy-1,2-diphenylethylamine, m.p. 166°-169°.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. washthe mixture was washed with 10% HCl (1 liter) and water
  5. dry with materialthe organic phase dried over MgSO4
  6. customThe solvent was evaporated to a solid residue which
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-92ba96571b0347b1a64043756c8e1223
Source dataset
uspto-grants-1985_05
Patent number
US04518779

Reaction notes

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