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

HRID 25072Notes

Reaction equation

HRID 25072 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25](=[S:28])[NH:26][NH2:27].[CH:29](OCC)(OCC)OCC.Cl>>[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[N:4][N:3]1[C:25]1[S:28][CH:29]=[N:27][N:26]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 12137411(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothiohydrazide

Product 1

HCID 22565507(+/-)-8-Methyl-5-(4-nitrophenyl)-7-(1,3,4-thiadiazol-2-yl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 77%

Procedure

A mixture of 0.57 g (1.43 mmol) of the starting material XVIII, 6 ml of triethyl orthoformate and a catalytic amount of hydrochloric acid was stirred at 80° C. for 1 h. After cooling the precipitated crystals were filtered off, washed with ethanol and dried to yield 0.45 g (77%) of the title compound; Mp.: 212-213° C.

Workup

  1. temperatureAfter cooling the precipitated crystals
  2. filtrationwere filtered off
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-88e5633eab164bc19133f4639fe81750
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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