Ammonia → 10,11-Dihydro-11-oxodibenzo[b,f]thiepin-3-carboxamide
Reaction equation
Cl[C:2]([C:4]1[CH:5]=[CH:6][C:7]2[C:13](=[O:14])[CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[S:9][C:8]=2[CH:19]=1)=[O:3].[NH3:20]>O1CCCC1>[O:14]=[C:13]1[CH2:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[S:9][C:8]2[CH:19]=[C:4]([C:2]([NH2:20])=[O:3])[CH:5]=[CH:6][C:7]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolve the acid chloride from Step 1 in 20 ml. of dry tetrahydrofuran and add this solution dropwise with stirring to a cooled (ice-bath) saturated solution of ammonia in 60 ml. of tetrahydrofuran. Pass ammonia through the reaction for 15 minutes. Stir at room temperature for an additional 15 minutes and evaporate the reaction mixture to dryness. Add a mixture of 12 ml. of ethanol and 60 ml. of water to the residue and stir at room temperature for an additional 30 minutes. Separate the solid by filtration and wash with water, then with ethanol and then with ether. Dry in vacuo to obtain the title product.
Workup
- stirringStir at room temperature for an additional 15 minutes
- customevaporate the reaction mixture to dryness
- additionAdd
- additiona mixture of 12 ml
- stirringof water to the residue and stir at room temperature for an additional 30 minutes
- customSeparate the solid
- filtrationby filtration
- washwash with water
- customDry in vacuo
Sources & evidence
- ORD record
- ord-9271f5f914104094b1d0ed9fbb4219c7
- Source dataset
- uspto-grants-1983_07
- Patent number
- US04394515
Reaction notes
Loading…