10,11-Dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepine → 10,11-Dihydro-10-(4-aminobenzoyl)dibenz[b,f][1,4]thiazepine

HRID 1938235Notes

Reaction equation

HRID 1938235 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[S:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[S:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 5457007210,11-Dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepineHCID 178418361HCID 178418361, compound

Product 1

HCID 5423000210,11-Dihydro-10-(4-aminobenzoyl)dibenz[b,f][1,4]thiazepineYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.2 g of 10,11-dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepine in 150 ml of methanol is shaken in a Parr hydrogenator under 50 pounds per square inch of hydrogen for 72 hours. The mixture is filtered through diatomaceous earth and the filtrate evaporated in vacuo. The residue is recrystallized from chloroform-hexane to give 1.8 g of crystals, m.p. 52°-55° C.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. customthe filtrate evaporated in vacuo
  3. customThe residue is recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-862e3b2ce9a64f5ca8110938894028a9
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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