Water → Flutazolam

HRID 597636Notes

Reaction equation

HRID 597636 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[C:11]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[O:19][CH2:20][CH2:21][N:10]2[CH2:9][C:8]1=[O:29])(=O)C.[OH-].[Na+].O>CO>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]2[N:7]([CH2:6][CH2:5][OH:4])[C:8](=[O:29])[CH2:9][N:10]3[CH2:21][CH2:20][O:19][C:11]3([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:12]=2[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21409990HCID 21409990, compound

Product 1

HCID 3398Flutazolam

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.5g (0.0012 M) of 7-(2-acetoxyethyl)-10-chloro-11b-(2-fluorophenyl)-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one in 5 ml of methanol was treated with 2 ml of 3N sodium hydroxide. After 3 hours, 50 ml of water was added and the solution was extracted with 40 ml of dichloromethane, which was then dried over anhydrous sodium sulfate and evaporated to dryness. The residue was crystallized from a mixture of methanol and water to give 10-chloro-11b-(2-fluorophenyl)-7-(2-hydroxyethyl)-2,3,5,11b-tetrahydrooxazolo(3,2-d)[1,4]benzodiazepin-6(7H)-one as white prisms, m.p. and m.m.p. 141°-146°.

Workup

  1. extractionthe solution was extracted with 40 ml of dichloromethane, which
  2. dry with materialwas then dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was crystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-080cb41f9b424dd4a17e8e5449b5c901
Source dataset
uspto-grants-1977_03
Patent number
US04014916

Reaction notes

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