Potassium Cyanide → HCID 19001264, compound
Reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]2[CH2:18][N:17]3[C:19]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[C:20]([CH3:25])[C:21]4[CH:22]=[CH:23][CH:24]=[C:15]([C:16]=43)[O:14]2)(=O)=O)=CC=1.[C-:35]#[N:36].[K+]>CS(C)=O>[C:35]([CH2:11][CH2:12][CH:13]1[CH2:18][N:17]2[C:19]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)=[C:20]([CH3:25])[C:21]3[CH:22]=[CH:23][CH:24]=[C:15]([C:16]=32)[O:14]1)#[N:36]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
13.7 9 of 2,3-dihydro-2-[2-(p-toluenesulfonyloxy)ethyl]-5-(4-methoxyphenyl)-6-methylpyrrolo[1,2,3-de]-1,4-benzoxazine (preparation see Example 1F)) were dissolved in 50 ml of hot dimethyl sulfoxide under a nitrogen atmosphere. 2.2 g of potassium cyanide were added to the reaction mixture heated at 80° C. and the mixture was stirred for a further 6 hours. For work-up, the reaction mixture was poured into ice-water after cooling. The resulting brown solid was filtered out and dissolved in dichloromethane. The organic solution was washed with water, dried and evaporated. The crude product remaining as a residue was purified by column chromatography using dichloromethane as an eluent. 9.1 g of 2,3-dihydro-2-(2-cyanoethyl)-5-(4-methoxyphenyl)-6-methyl-pyrrolo[1,2,3-de]-1,4-benzoxazine were obtained as a white solid having a melting point of 113° to 14° C.
Workup
- temperatureafter cooling
- filtrationThe resulting brown solid was filtered out
- dissolutiondissolved in dichloromethane
- washThe organic solution was washed with water
- customdried
- customevaporated
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-ac3447f35c6b40e3ad4dfc29e1c1803d
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05474988
Reaction notes
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