Acetic Anhydride → 2-Acetamido-4-fluorotoluene

HRID 1106229Notes

Reaction equation

HRID 1106229 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH3:16]>O>[C:5]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH3:16])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 677745-Fluoro-o-toluidine

Product 1

HCID 35231182-Acetamido-4-fluorotoluene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

139 ml (150.4 g; 1.473 molecules) of acetic anhydride were added in one portion to a hot (35° ) stirred mixture of 90.0 g (0.719 molecule) of 2-amino-4-fluorotoluene (1) in 513 ml of water. The temperature rose to 73° and a solid separated out (by precipitation). The mixture was cooled to ambient temperature and the solid was recovered on a filter, washed with water (525 ml), then dried in vacuo at 80°, yield: 115.7 g (96.2%); m.p.: 127°-128°. The material was still transformable.

Workup

  1. customrose to 73°
  2. customa solid separated out (by precipitation)
  3. customthe solid was recovered on a filter
  4. washwashed with water (525 ml)
  5. customdried in vacuo at 80°

Sources & evidence

ORD record
ord-2df4915d69f94b4eba49365d1c73085f
Source dataset
uspto-grants-1982_01
Patent number
US04312862

Reaction notes

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