Diisopropyl Ether → HCID 21701380, compound

HRID 1596351Notes

Reaction equation

HRID 1596351 reaction equation
[Cl:1][C:2]1[C:12]2[NH:11][C:10](=[O:13])[CH2:9][N+:8]([O-])=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(OC(C)C)(C)C.[C:29]([O:32]C(=O)C)(=[O:31])[CH3:30]>>[C:29]([O:32][CH:9]1[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:12]=2[NH:11][C:10]1=[O:13])(=[O:31])[CH3:30]

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 178516820HCID 178516820, compound

Product 1

HCID 21701380HCID 21701380, compoundYield 50%

Procedure

A suspension of 9-chloro-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-4-oxide (1.475 g) in acetic anhydride (12 ml) was refluxed for 0.5 hour. The resultant clear solution was cooled in an ice-bath to afford precipitate. To the cooled suspension was added diisopropyl ether (20 ml) and the mixture was cooled further. The resultant precipitate was collected by filtration and washed with diisopropyl ether to give (3RS)-3-acetoxy-5-(2-fluorophenyl)-9-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (0.84 g, 50.0% yield) as a colorless crystalline powder.

Workup

  1. temperaturewas refluxed for 0.5 hour
  2. temperatureThe resultant clear solution was cooled in an ice-bath
  3. customto afford precipitate
  4. temperaturethe mixture was cooled further
  5. filtrationThe resultant precipitate was collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-f0119a3718244377a9dc56f1fe80e37b
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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