Acetic Acid → (+/-)-7-(4-Carboxythiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25081Notes

Reaction equation

HRID 25081 reaction equation
C(O)C.C([O:6][C:7]([C:9]1[N:10]=[C:11]([N:14]2[CH:20]([CH3:21])[CH2:19][C:18]3[CH:22]=[C:23]4[O:28][CH2:27][O:26][C:24]4=[CH:25][C:17]=3[C:16]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)=[N:15]2)[S:12][CH:13]=1)=[O:8])C.[OH-].[Na+].C(O)(=O)C>O>[C:7]([C:9]1[N:10]=[C:11]([N:14]2[CH:20]([CH3:21])[CH2:19][C:18]3[CH:22]=[C:23]4[O:28][CH2:27][O:26][C:24]4=[CH:25][C:17]=3[C:16]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)=[N:15]2)[S:12][CH:13]=1)([OH:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 12137427(+/-)-7-(4-Ethoxycarbonyl-thiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Product 1

HCID 22565444(+/-)-7-(4-Carboxythiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9 ml of ethanol, 0.85 g (1.89 mmol) of (±)-7-(4-ethoxycarbonyl-thiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (Example 8) and 7 ml of 1N sodium hydroxide solution was stirred at 90° C. After cooling, it was acidified with acetic acid, diluted with water and the precipitated crystals were filtered off, washed with water and dried to yield 0.78 g (98%) of the title compound; Mp.: >260° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals were filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4aac4ab194e646d7843ff9944d0c4efa
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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