Sulfuric Acid → HCID 21873086, compound

HRID 614865Notes

Reaction equation

HRID 614865 reaction equation
[Cl:1][CH2:2][C:3]#[N:4].[Cl:5][C:6]([Cl:19])([Cl:18])[CH:7](O)[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)[OH:21]>>[Cl:5][C:6]([Cl:19])([Cl:18])[CH:7]([NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:4][C:3](=[O:21])[CH2:2][Cl:1]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 39323N-(2,2,2-trichloro-1-hydroxyethyl)benzamide

Product 1

HCID 21873086HCID 21873086, compound

Procedure

Chloroacetonitrile (4.1g) was added dropwise to a solution of 1,1,1-trichloro-2-hydroxy-2-benzamidoethane (13.4g) in concentrated sulphuric acid (50 ml). The temperature was kept at 0° during the addition. The mixture was stirred at room temperature for 4 hours, then left overnight. The reaction mixture was poured on to ice. The precipitated solid was collected, washed with water and dried (14.65g). Recrystallisation from nitromethane gave pure 1,1,1-trichloro-2-benzamido-2-(chloroacetamido)ethane (12.7g, m.p. 210°-12°) whose infra red spectrum was identical to that of the product of the preceding Example.

Workup

  1. additionThe temperature was kept at 0° during the addition
  2. waitleft overnight
  3. additionThe reaction mixture was poured on to ice
  4. customThe precipitated solid was collected
  5. washwashed with water
  6. customdried (14.65g)
  7. customRecrystallisation from nitromethane

Sources & evidence

ORD record
ord-5ae4b272ea484b8a8dfd91e618d5b1b1
Source dataset
uspto-grants-1979_03
Patent number
US04146646

Reaction notes

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