Water → HCID 12703747, compound

HRID 1763942Notes

Reaction equation

HRID 1763942 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][N:10]=2)=[CH:5][CH:4]=1)=O.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.B(O)(O)O.O>C1(C)C(C)=CC=CC=1>[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]=[CH:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[O:11][N:10]=3)=[CH:5][CH:4]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7628Boric AcidHCID 78124-ChloroanilineHCID 18357635HCID 18357635, compound

Product 1

HCID 12703747HCID 12703747, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

22.32 g of 3-(p-formylphenyl)-1,2-benzisoxazole, 14.03 g of p-chloroaniline and 0.5 g of boric acid in 160 ml of xylene are refluxed for 2 hours, the water formed being distilled off. The mixture is cooled to 60° C., 500 ml of methanol are added and the resulting mixture is further cooled to -10° C. The product which has precipitated is filtered off with suction, washed with 100 ml of cold methanol and dried. This gives 32 g (96.2% of theory) of compound (102) in the form of pale yellow crystals which melt at 164° to 165° C. After recrystallising twice from toluene, pale yellow crystals with a melting point of 164.5° to 165° C. are obtained.

Workup

  1. distillationbeing distilled off
  2. addition500 ml of methanol are added
  3. temperaturethe resulting mixture is further cooled to -10° C
  4. customThe product which has precipitated
  5. filtrationis filtered off with suction
  6. washwashed with 100 ml of cold methanol
  7. customdried
  8. custommelt at 164° to 165° C
  9. customAfter recrystallising twice from toluene, pale yellow crystals with a melting point of 164.5° to 165° C.
  10. customare obtained

Sources & evidence

ORD record
ord-e214c028425d4bd1a729bd8acac29ee4
Source dataset
uspto-grants-1978_09
Patent number
US04113938

Reaction notes

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