Benzyl Bromide → HCID 21511899, compound

HRID 1576322Notes

Reaction equation

HRID 1576322 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[N:8]3[CH2:15][CH2:16][O:17][C:7]3([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[N:10]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:9](=[O:14])[N:8]3[CH2:15][CH2:16][O:17][C:7]3([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 21511885HCID 21511885, compound

Product 1

HCID 21511899HCID 21511899, compoundYield 83.4%

Conditions

Temperature
60 °C

Procedure

To a solution of 0.93 g of 9-nitro-2,3,6,10b-tetrahydro-10b-phenyl-5H-oxazolo[3,2-C]quinazolin-5-one in 10 ml. of dimethylfomamide was added 0.18 g of 52.9% sodium hydride. The mixture was stirred with heating at 60°C for 1 hr. then, 0.68 g of benzyl bromide was added thereto. The resulting mixture was heated at 100°C for 4 hours. After cooling, the reaction mixture was poured into 50 ml. of water and the resulting precipitates were collected by filtration, washed with water and dried. The crude product was recrystallized from a mixture of methanol and carbon tetrachloride to give 1.0 g of 9-nitro-2,3,6,10b-tetrahydro-6-benzyl-10b-phenyl-5H-oxazolo[3,2-C]quinazolin-5-one as yellowish brown prisms, having a melting point of 96°-98°C (decomp.).

Workup

  1. temperatureThe resulting mixture was heated at 100°C for 4 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured into 50 ml
  4. customof water and the resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe crude product was recrystallized from a mixture of methanol and carbon tetrachloride

Sources & evidence

ORD record
ord-04663eb65519407ab9db34a518a9f717
Source dataset
uspto-grants-1976_09
Patent number
US03980645

Reaction notes

Loading…