Sulfur → HCID 19012243, compound

HRID 1729239Notes

Reaction equation

HRID 1729239 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[NH:21][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]2[N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]=4[C:8]=2[CH2:7]1)[CH2:13][CH2:12][CH2:11]3)=[O:5])[CH3:2].[S]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]2[N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]=4[C:8]=2[CH:7]=1)[CH2:13][CH2:12][CH2:11]3)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5362487Sulfur2×HCID 19012257HCID 19012257, compound

Product 1

HCID 19012243HCID 19012243, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3.6 g (10 mmol) of 10-ethoxycarbonyl-8-phenyl-5,6,8,9,10,11-hexahydro-4H-pyrido[4',3':4,5]pyrrolo[3,2,1-ij]quinoline (a mixture of isomers), obtained analogously to the method of example I a) to c) were boiled while stirring for 8 hours together with 0.8 g (25 mmol) of sulphur in 25 ml of xylene. Another 0.2 g of sulphur were added and boiling with stirring was carried out for another 8 hours. The reaction mixture was evaporated in vacuum and chromatographed over 150 g of silicagel using methylene chloride with 10% by volume of ethyl acetate as an eluent. The desired fraction was evaporated in vacuum. The residue was crystallised from 10 ml of ethyl acetate. 2.1 g (59%) of the desired product were obtained having a melting-point of 173°-174° C,

Workup

  1. customobtained analogously to the method of example I a) to c)
  2. customThe reaction mixture was evaporated in vacuum
  3. customchromatographed over 150 g of silicagel
  4. customThe desired fraction was evaporated in vacuum
  5. customThe residue was crystallised from 10 ml of ethyl acetate

Sources & evidence

ORD record
ord-c791ceb1bc1a403c878313386700efec
Source dataset
uspto-grants-1994_07
Patent number
US05332746

Reaction notes

Loading…