Gyki 52895 → Gyki-53405

HRID 440801Notes

Reaction equation

HRID 440801 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][CH:11]([CH3:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(N(CC)CC)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][CH:11]([CH3:22])[N:10]([C:27](=[O:29])[CH3:28])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3539Gyki 52895HCID 6212ChloroformHCID 7918Acetic Anhydride

Product 1

HCID 126756Gyki-53405Yield 85.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 3.58 g (12.1 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine in 100 ml of chloroform first 1.68 ml (12.1 mmol) of triethylamine,-then under constant ice-cooling and stirring 1.15 ml (12.1 mmol) of acetic anhydride were added. Stirring was continued for additional 2 hours, then the solution was extracted with 3×100 ml of water, the organic layer was dried and evaporated under reduced pressure. The crystalline residue was recrystallized from 40 ml of isopropanol to obtain 3.50 g (85.7%) of the aimed product, m.p. 220°-222° C. After repeated recrystallization the m.p. increased to 223°-225° C.

Workup

  1. additionwere added
  2. extractionthe solution was extracted with 3×100 ml of water
  3. customthe organic layer was dried
  4. customevaporated under reduced pressure
  5. customThe crystalline residue was recrystallized from 40 ml of isopropanol

Sources & evidence

ORD record
ord-f3a67b8b0db34cd78d46f1b4b02c0f55
Source dataset
uspto-grants-1996_05
Patent number
US05521174

Reaction notes

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