Chloroacetyl chloride → HCID 20283268, compound

HRID 463346Notes

Reaction equation

HRID 463346 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18](CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[Cl:23][CH2:24][C:25]([NH:18][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:8])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 775752,2-Diphenylethylamine

Product 1

HCID 20283268HCID 20283268, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2,2-diphenylethylamine (100.0 g, 0.5 m) and triethylamine (123.0 g, 1.2 m) in chloroform (2 liters) maintained under nitrogen at ambient temperature was added dropwise chloroacetylchloride (124.2 g, 1.1 m) and the mixture stirred for 2 hours. Thin layer chromatography (TLC) analysis showed the reaction to be complete. The mixture was transferred to a separatory funnel and washed with 10% HCl (3×1 liter) and water (1 liter) and the organic phase dried over MgSO4. The solvent was evaporated to a dark oil which was treated with cyclohexane (1 liter) and, upon standing, a solid crystallized which was collected by filtration, washed with cyclohexane and air dried to give 122.0 g of N-chloroacetyl-1,1-diphenylethylamine as a tan solid, m.p. 73°-74°.

Workup

  1. customthe reaction
  2. customThe mixture was transferred to a separatory funnel
  3. washwashed with 10% HCl (3×1 liter) and water (1 liter)
  4. dry with materialthe organic phase dried over MgSO4
  5. customThe solvent was evaporated to a dark oil which
  6. additionwas treated with cyclohexane (1 liter)
  7. customa solid crystallized which
  8. filtrationwas collected by filtration
  9. washwashed with cyclohexane and air
  10. customdried

Sources & evidence

ORD record
ord-bf4fb4d265f14583b0884c0abfc1569d
Source dataset
uspto-grants-1985_05
Patent number
US04518779

Reaction notes

Loading…