Formic Acid → HCID 15290896, compound
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][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH:38](O)=[O:39]>ClCCl>[CH:38]([NH: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][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1)=[O:39]Participants
Procedure
3.0 g (10.2 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine were dissolved in 160 ml of dichloromethane and first 2.75 g (13.3 mmol) of dicyclohexylcarbodiimide, then 0.51 ml (13.3 mmol) of 100% formic acid were added and the reaction mixture was stirred for 2 hours at room temperature. The precipitated N,N'-dicyclohexylurea was filtered, the filtrate was extracted with 2×30 ml of 10% aqueous sodium carbonate solution, then with 2×30 ml of distilled water, the organic layer was dried and evaporated at reduced pressure. The residue was dissolved in ethyl acetate, filtered and evaporated under reduced pressure. The resulting raw product was recrystallized from 20 ml of 50% ethanol to yield 2.93 g (89.3%) of the aimed product, m.p. 152°-154° C. (slight decomp.).
Workup
- filtrationThe precipitated N,N'-dicyclohexylurea was filtered
- extractionthe filtrate was extracted with 2×30 ml of 10% aqueous sodium carbonate solution
- dry with materialwith 2×30 ml of distilled water, the organic layer was dried
- customevaporated at reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- filtrationfiltered
- customevaporated under reduced pressure
- customThe resulting raw product was recrystallized from 20 ml of 50% ethanol
Sources & evidence
- ORD record
- ord-e580d803be9b4436a553cbb6ac4a868f
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05519019
Reaction notes
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