p-Toluenesulfonic acid → 2-[2-(4-Chloroanilino)-5-benzoxazolyl]propionitrile

HRID 866562Notes

Reaction equation

HRID 866562 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:19]([CH3:22])[C:20]#[N:21])[CH:15]=[CH:16][C:17]=1O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][C:17]3[CH:16]=[CH:15][C:14]([CH:19]([CH3:22])[C:20]#[N:21])=[CH:13][C:12]=3[N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 76934-Chlorophenyl IsocyanateHCID 122026362-(3-Amino-4-hydroxyphenyl)propanenitrile

Product 1

HCID 203195992-[2-(4-Chloroanilino)-5-benzoxazolyl]propionitrile

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-chlorophenylisocyanate (3.1 g.) was slowly added to a stirred solution of 2-(3-amino-4-hydroxyphenyl propionitrile (3.3 g) in xylene (35 ml.) at room temperature. When the addition was complete p-toluenesulphonic acid (250 mg.) was added, and the solution was heated under reflux using a Dean and Stark apparatus. On cooling, the solution was washed with aqueous sodium bicarbonate solution and evaporated to dryness. The residue was recrystallised to give 2-[2-(4-chloroanilino)-5-benzoxazolyl] propionitrile as a creme solid which was characterised by n.m.r. spectroscopy.

Workup

  1. additionWhen the addition
  2. additionwas added
  3. temperaturethe solution was heated
  4. temperatureunder reflux
  5. temperatureOn cooling
  6. washthe solution was washed with aqueous sodium bicarbonate solution
  7. customevaporated to dryness
  8. customThe residue was recrystallised

Sources & evidence

ORD record
ord-4f38cf89905448688a3c5d1ed0a9690e
Source dataset
uspto-grants-1978_07
Patent number
US04100168

Reaction notes

Loading…