Water → 3-{(dibenzo[b,e]thiepin-11(6H)-yliden)-amino}-propyl tosylate
Reaction equation
[CH:1]1[C:11]2[C:10](=[N:12][CH2:13][CH2:14][CH2:15][OH:16])[C:9]3[CH:17]=[CH:18][CH:19]=[CH:20][C:8]=3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>C(Cl)Cl>[S:33]([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)([O:16][CH2:15][CH2:14][CH2:13][N:12]=[C:10]1[C:9]2[CH:17]=[CH:18][CH:19]=[CH:20][C:8]=2[CH2:7][S:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]1=2)(=[O:35])=[O:34]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
10.0 G. of 3-{ (dibenzo[b,e]thiepin-11(6H)-yliden)-amino}-1-propanol in 30 ml. of absolute pyridine are treated at 0° C. within 1 hour with 9.0 g. of p-toluenesulfonyl chloride. The solution is stirred at 0° C. for 1 hour and subsequently left to stand at 0° C. for 16 hours. The mixture is then diluted with methylene chloride and treated with water. The organic phase is washed with aqueous sodium bicarbonate solution, dried over sodium sulfate and evaporated under reduced pressure. There is obtained crude 3-{(dibenzo[b,e]thiepin-11(6H)-yliden)-amino}-propyl tosylate which is used in the reaction described in the first paragraph of this Example without further purification.
Workup
- waitsubsequently left
- waitto stand at 0° C. for 16 hours
- washThe organic phase is washed with aqueous sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-f3545eb9b7eb45fdab7dbf64e8545a83
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03985895
Reaction notes
Loading…