Sulfuric Acid → HCID 21873086, compound

HRID 614864Notes

Reaction equation

HRID 614864 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]([Cl:19])([Cl:18])[CH:11](O)[NH:12][C:13](=[O:16])[CH2:14][Cl:15].S(=O)(=O)(O)[OH:21]>>[Cl:9][C:10]([Cl:18])([Cl:19])[CH:11]([NH:8][C:1](=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:12][C:13](=[O:16])[CH2:14][Cl:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 2377552-chloro-n-(2,2,2-trichloro-1-hydroxyethyl)acetamide

Product 1

HCID 21873086HCID 21873086, compound

Procedure

Benzonitrile (5.2g) was added dropwise to a solution of 1,1,1-trichloro-2-hydroxy-2-(chloroacetamido)ethane (12.05g) 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 (19.6g). Recrystallisation from nitromethane gave pure 1,1,1-trichloro-2-benzamido-2-(chloroacetamido)ethane (14.6g, m.p. 210°-12°)

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 (19.6g)
  7. customRecrystallisation from nitromethane

Sources & evidence

ORD record
ord-1f275db62ab7438eb7564c81a5db82cd
Source dataset
uspto-grants-1979_03
Patent number
US04146646

Reaction notes

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