4-Hydroxybenzoic acid hydrazide → HCID 135736241, compound

HRID 986500Notes

Reaction equation

HRID 986500 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:5]=1[C:6]#[N:7])=[C:2]=[O:3].[OH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([NH:20][NH2:21])=O)=[CH:16][CH:15]=1.C(N(CC)CC)C>CS(O)(=O)=O.C(O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:4]2[NH:1][C:2](=[O:3])[N:21]3[N:20]=[C:18]([C:17]4[CH:22]=[CH:23][C:14]([OH:13])=[CH:15][CH:16]=4)[N:7]=[C:6]3[C:5]=2[CH:8]=1

Participants

6

Reactant 3

HCID 17424-Hydroxybenzoic acid hydrazideHCID 8471TriethylamineHCID 38501365-chloro-2-isocyanatobenzonitrile

Product 1

HCID 135736241HCID 135736241, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 702EthanolSolvent

Procedure

The intermediate prepared from 2-isocyanato-5-chlorobenzonitrile (6.1 g) and 4-hydroxybenzoylhydrazine (7.0 g) in 53% yield as described in Example 23 is added to a mixture of triethylamine (31 ml), methanesulphonic acid (25 drops) and ethanol (300 ml) and stirred at reflux under nitrogen for two hours. The reaction mixture is concentrated to dryness at reduced pressure, redissolved in ethanol and treated with water. The solid is collected, washed with water and dried under high vacuum to afford pure 9-chloro-2-(4-hydroxy-phenyl)-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one, mp>350°

Workup

  1. temperatureat reflux under nitrogen for two hours
  2. concentrationThe reaction mixture is concentrated to dryness at reduced pressure
  3. dissolutionredissolved in ethanol
  4. additiontreated with water
  5. customThe solid is collected
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-91859b5f74a348e99a73c81a09e7dae5
Source dataset
uspto-grants-1987_12
Patent number
US04713383

Reaction notes

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