p-Toluenesulfonic acid → HCID 67858272, compound

HRID 703439Notes

Reaction equation

HRID 703439 reaction equation
[CH2:1]1[N:12]2[C:13]3[C:3](=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=S)[NH:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[CH2:2]1.[CH2:19]([NH2:22])[C:20]#C.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CCC>[CH3:23][C:15]1[CH:16]=[CH:17][C:10]2[N:9]3[CH:20]=[CH:19][N:22]=[C:8]3[C:7]3[CH2:6][CH2:5][CH:4]=[C:3]4[CH:2]=[CH:1][N:12]([C:13]=34)[C:11]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 239041PropargylamineHCID 15132539HCID 15132539, compound

Product 1

HCID 67858272HCID 67858272, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1,2-Dihyrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-thione (4 g), propargylamine (1.2 ml), n-butanol (100 ml) and a catalytic amount of p-toluenesulfonic acid were combined and refluxed overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2% methanol/dichloromethane) to give 3.1 g (71.4%) of product. Recrystallization from ethanol gave the analytical sample, mp 175° C.

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by high performance liquid chromatography (2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-47277336e2e84e2ea84afb7be88cab6a
Source dataset
uspto-grants-1991_01
Patent number
US04983601

Reaction notes

Loading…