Hydrogen Sulfide → HCID 21825599, compound

HRID 917828Notes

Reaction equation

HRID 917828 reaction equation
[SH2:1].[C:2]([C:4]1[CH:8]=[N:7][N:6]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[N:5]=1)#[N:3].C(N(CC)CC)C>C(O)C>[C:12]([O:11][C@@H:10]1[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:21][C@H:9]1[N:6]1[N:5]=[C:4]([C:2](=[S:1])[NH2:3])[CH:8]=[N:7]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 8471TriethylamineHCID 21825597HCID 21825597, compound

Product 1

HCID 21825599HCID 21825599, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen sulfide was passed through a suspension of 2.0 g of 7 in ethanol (60 ml) to which 3.5 ml of triethylamine had been added. After 2 1/2 hr passage of hydrogen sulfide was ceased and the solvent was removed. The resultant syrup was dissolved in a minimum of chloroform and added to a silica gel column (2 × 38 cm) packed in chloroform. The column was eluted with chloroform (0.25 liter) and chloroform-ethyl acetate (9:1, 0.5 liter); 20 ml fractions were collected. Fractions 19-34 provided 2.6 g (98%) of 9 as a syrup; nmr (DMSO-d6) δ 6.36 (d, 1, J1',2' 2.0 Hz, 1'--H), 8.39 (s, 1,5--H); (CDCl3) δ 6.24 (d, 1, J1'2' 3.0 Hz, 1'--H), 8.32 (s, 1, 5--H).

Workup

  1. additionhad been added
  2. customthe solvent was removed
  3. dissolutionThe resultant syrup was dissolved in a minimum of chloroform
  4. additionadded to a silica gel column (2 × 38 cm)
  5. washThe column was eluted with chloroform (0.25 liter) and chloroform-ethyl acetate (9:1, 0.5 liter)
  6. custom20 ml fractions were collected

Sources & evidence

ORD record
ord-176a3748c5814d3ea8da33e248a5d71f
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

Loading…