Carbon Disulfide → HCID 131717959, compound

HRID 2209995Notes

Reaction equation

HRID 2209995 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=3)[N:15]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:14]=2)[CH2:9][CH2:8]1.[C:30](=S)=[S:31]>ClCCl.CO>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21]([C:13]([CH:10]3[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][N:4]4[CH2:3][CH2:2][NH:1][C:30]4=[S:31])[CH2:8][CH2:9]3)=[CH:14][N:15]2[C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 19379849HCID 19379849, compound

Product 1

HCID 131717959HCID 131717959, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of compound 11a (4.5 g) in dichloromethane/methanol 1:1 (100 ml) was added 5 ml of carbondisulfide. The mixture was left at room temperature for one hour. Then the solvents were evaporated and finally the remaining viscous oil was heated at 130°-140° C. in solution in 1-pentanol. When the evolution of H2S had ceased the solvents were evaporated. The resulting oil was purified by column chromatography on silica gel (eluted with ethyl acetate/methanol 1:1) yielding 2 g of the title compound 12a as a crystalline base. Mp: 184-186° C.

Workup

  1. customThen the solvents were evaporated
  2. temperaturefinally the remaining viscous oil was heated at 130°-140° C. in solution in 1-pentanol
  3. customwere evaporated
  4. customThe resulting oil was purified by column chromatography on silica gel (eluted with ethyl acetate/methanol 1:1)

Sources & evidence

ORD record
ord-646f90a6d74e426eaf44f0eaf28684b8
Source dataset
uspto-grants-1995_10
Patent number
US05457115

Reaction notes

Loading…