Acetic Acid → HCID 178507587, compound

HRID 1786168Notes

Reaction equation

HRID 1786168 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8]C(=O)[N:6]3[N:13]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[N:15]=[C:5]3[C:4]=2[CH:3]=1.[OH-].[Na+].O.C(O)(=O)C>C(O)CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:8])=[C:4]([C:5]2[NH:6][N:13]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[N:15]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 1363323169-chloro-2-cyclopropyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one

Product 1

HCID 178507587HCID 178507587, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a well stirred slurry of 9-chloro-2-cyclopropyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (5.20 g, 19.9 mmol) in ethylene glycol (40 mL) which was heated to 100° C. was added aqueous sodium hydroxide (10 N, 4 mL, 39.9 mmol). The slurry was heated at reflux for 18 h. After cooling, water (25 mL) was added to the resulted suspension and the pH was adjusted to 6-7 by adding glacial acetic acid (CO2-evolution). The slurry was stirred for 30 min. The solid was collected by filtration and washed with water (3×15 mL). Drying (HV) afforded the title compound (4.05 g, 86%) as a light brown solid. MS: m/e=235.0 [M+H]+.

Workup

  1. temperatureThe slurry was heated
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (3×15 mL)
  6. customDrying (HV)

Sources & evidence

ORD record
ord-9b4abc04cd214ce2aeb75a4d102e3819
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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