Benzoyl chloride → HCID 21873086, compound

HRID 614861Notes

Reaction equation

HRID 614861 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]([Cl:20])([Cl:19])[CH:12]([NH2:18])[NH:13][C:14](=[O:17])[CH2:15][Cl:16].C(N(CC)CC)C>CC(C)=O>[Cl:10][C:11]([Cl:19])([Cl:20])[CH:12]([NH:18][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:13][C:14](=[O:17])[CH2:15][Cl:16]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53803331HCID 53803331, compound

Product 1

HCID 21873086HCID 21873086, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Benzoyl chloride (4.7g) in acetone (5ml) was added dropwise to a solution of 1,1,1-trichloro-2-amino-2-(chloroacetamido)ethane (8g) in acetone (50ml) containing triethylamine (3.4g). The temperature rose to 50°. The mixture was stirred for 2 hours. The salt was filtered off and the filtrate poured into water. The solid formed was collected, washed with water and dried (10g). Recrystallisation from nitromethane gave pure 1,1,1-trichloro-2-benzamido-2-(chloroacetamido)ethane (8.7g. m.p. 211°-213°).

Workup

  1. customrose to 50°
  2. filtrationThe salt was filtered off
  3. additionthe filtrate poured into water
  4. customThe solid formed
  5. customwas collected
  6. washwashed with water
  7. dry with materialdried (10g)
  8. customRecrystallisation from nitromethane

Sources & evidence

ORD record
ord-823455765c3649189f32ac5781a7902e
Source dataset
uspto-grants-1979_03
Patent number
US04146646

Reaction notes

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