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Water → 3-{(dibenzo[b,e]thiepin-11(6H)-yliden)-amino}-propyl tosylate

HRID 1287922
Notes
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Reaction equation

HRID 1287922 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 215070363-{(dibenzo[b,e]-thiepin-11(6H)-yliden)-amino}-1-propanol

Product 1

HCID 215070443-{(dibenzo[b,e]thiepin-11(6H)-yliden)-amino}-propyl tosylate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

  1. waitsubsequently left
  2. waitto stand at 0° C. for 16 hours
  3. washThe organic phase is washed with aqueous sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f3545eb9b7eb45fdab7dbf64e8545a83
Source dataset
uspto-grants-1976_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03985895

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes