Hydrogen Sulfide → HCID 178519008, compound

HRID 610612Notes

Reaction equation

HRID 610612 reaction equation
C(N[C:9]1[CH2:17][CH2:16][CH2:15][CH2:14][C:10]=1[C:11]([NH2:13])=[O:12])C1C=CC=CC=1.[SH2:18]>C(O)(=O)C>[OH:12][C:11]1[C:10]2[CH2:14][CH2:15][CH2:16][CH2:17][C:9]=2[S:18][N:13]=1

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 106571002-(Benzylamino)-3,4,5,6-tetrahydrobenzamide

Product 1

HCID 178519008HCID 178519008, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-benzylamino-3,4,5,6-tetrahydrobenzamide 21a (15 g) in glacial acetic acid (100 mL) was added excess hydrogen sulfide at 80° C. for 4 h. The reaction mixture was evaporated and ether was added to the residue which afforded crystallisation. The crystals were dissolved in ethyl acetate (30 mL) and a solution of bromine (8.3 mL) in ethyl acetate (30 mL) was dropwise added at room temperature. The mixture was stirred for 20 h at room temperature and evaporated. Column chromatography on silica gel (eluent:ethyl acetate-ethanol 1:1 containing 1% glacial acetic acid) gave the title compound (3.3 g): mp 157-158° C.

Workup

  1. customThe reaction mixture was evaporated
  2. additionether was added to the residue which
  3. customafforded
  4. customcrystallisation
  5. dissolutionThe crystals were dissolved in ethyl acetate (30 mL)
  6. additiona solution of bromine (8.3 mL) in ethyl acetate (30 mL) was dropwise added at room temperature
  7. customevaporated

Sources & evidence

ORD record
ord-5756fdafaf04494883e5753df9312e9c
Source dataset
uspto-grants-1999_12
Patent number
US05998613

Reaction notes

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