Aniline → Chloroacetanilide

HRID 1283942Notes

Reaction equation

HRID 1283942 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:10][CH2:11][C:12](Cl)=[O:13]>C1(C)C=CC=CC=1>[Cl:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 6115AnilineHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 11485Chloroacetanilide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Aniline (93.1 g; 1.00 mole) was dissolved in toluene (750 ml), 10 % NaOH (750 ml) was added and the stirred mixture was cooled to 0°C. Chloroacetyl chloride (197 g; 1.75 mole) was added dropwise during 45 minutes while keeping the temperature below 10°C. Stirring was continued at room temperature for about one hour. The precipitated crystalline 2-chloro-N-phenylacetamide was filtered off, washed on the filter with cold toluene and dried in vacuo at 60°C. Yield: 151 g (90.0 %); m.p. 134°-136°C.

Workup

  1. customthe temperature below 10°C
  2. filtrationThe precipitated crystalline 2-chloro-N-phenylacetamide was filtered off
  3. washwashed on the
  4. filtrationfilter with cold toluene
  5. customdried in vacuo at 60°C

Sources & evidence

ORD record
ord-ba104dd30df14992aa89f3837e851e5a
Source dataset
uspto-grants-1976_08
Patent number
US03976771

Reaction notes

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