Chloroacetyl chloride → HCID 12777162, compound

HRID 1638474Notes

Reaction equation

HRID 1638474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([C:17](=[O:18])[CH2:16][Cl:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 75453-Chlorodiphenylamine

Product 1

HCID 12777162HCID 12777162, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

N-(3-Chlorophenyl)aniline (25.1 g, 0.123 mole) and chloroacetyl chloride (19.6 ml, 0.246 mole) were refluxed in toluene (100 ml) for 4 hours, then stripped of toluene and excess acid chloride in vacuo to yield an oil which crystallized on scratching. Recrystallization from ethanol/H2O gave purified title product, 32.6 g, m.p. 94°-96.5°.

Workup

  1. customto yield an oil which
  2. customcrystallized
  3. customRecrystallization from ethanol/H2O
  4. customgave
  5. custompurified title product, 32.6 g, m.p. 94°-96.5°

Sources & evidence

ORD record
ord-94e2bb9448f943a98ae3ed2ccac219d8
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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