HCID 1089054, compound → HCID 136006861, compound

HRID 2052280Notes

Reaction equation

HRID 2052280 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][N:14]=[C:7]1[N:6]=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][N:14]=[C:7]1[NH:6][CH:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 1089054HCID 1089054, compoundHCID 4311764Sodium borohydride

Product 1

HCID 136006861HCID 136006861, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2.6 g of 7-chloro-5-phenyl-s-triazolo[4,3-a]quinazoline in 100 ml of dimethylformamide was added 1 g of sodium borohydride. The mixture was stirred at room temperature overnight and then poured into ice-water. The resulting precipitate was collected by filtration, washed with water and dried. The so obtained solid was suspended in a mixture of 30 ml of methanol and 30 ml of concentrated hydrochloric acid, and the mixture was heated under reflux for 40 minutes. After cooling, the resulting mixture was neutralized with ammonia water. The precipitate formed was collected by filtration, washed with water, and recrystallized from methanol to give 1.2 g of 7-chloro-4,5-dihydro-5-phenyl-s-triazolo[4,3-a]quinazoline as colorless prisms, m.p. 241.5°-243.5° C.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. additionThe so obtained solid was suspended in a mixture of 30 ml of methanol and 30 ml of concentrated hydrochloric acid
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 40 minutes
  7. temperatureAfter cooling
  8. customThe precipitate formed
  9. filtrationwas collected by filtration
  10. washwashed with water
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-feaafe6cbb68417489bf69e93c5f923d
Source dataset
uspto-grants-1980_01
Patent number
US04183932

Reaction notes

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