Water → HCID 12401527, compound

HRID 1763940Notes

Reaction equation

HRID 1763940 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1)=O.[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21].B(O)(O)O.O>C1(C)C(C)=CC=CC=1>[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[N:21]=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72402-ChloroanilineHCID 7628Boric AcidHCID 12401526HCID 12401526, compound

Product 1

HCID 12401527HCID 12401527, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

22.32 g of 2-(p-formylphenyl)-s-triazolo[1,5-a]pyridine (II), 14.03 g of o-chloroaniline and 1 g of boric acid in 350 ml of xylene are refluxed for 2 hours, the water formed being distilled off. The mixture is cooled to 60° C., 450 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 26.3 g (79.1% of theory) of compound (101) in the form of a pale beige powder with a melting point of 135° to 136° C. After recrystallising twice from methanol, 22.2 g (66.7% of theory) of small, pale yellow, glossy needles with a melting point of 135° to 136° C. are obtained.

Workup

  1. distillationbeing distilled off
  2. addition450 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. customAfter recrystallising twice from methanol, 22.2 g (66.7% of theory) of small, pale yellow, glossy needles with a melting point of 135° to 136° C.
  9. customare obtained

Sources & evidence

ORD record
ord-6e7b2c53d8cb4118b7be9be3cee4664a
Source dataset
uspto-grants-1978_09
Patent number
US04113937

Reaction notes

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