Hydrogen Sulfide → HCID 9821811, compound

HRID 47287Notes

Reaction equation

HRID 47287 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6](CCC2C(Cl)=CC=CC=2C(N)=S)[CH:7]=1.[SH2:22].BrC1C=CC(OC)=C(C[CH2:31][C:32]2[C:39](Cl)=[CH:38][CH:37]=[CH:36][C:33]=2[C:34]#[N:35])C=1>C(O)C.C(N(CC)CC)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([S:22][CH2:31][C:32]2[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=2[C:34]2[NH:35][CH2:32][CH2:33][CH2:34][N:35]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 402Hydrogen SulfideHCID 22744769HCID 22744769, compoundHCID 22744933HCID 22744933, compound

Product 1

HCID 9821811HCID 9821811, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

9, 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-thiobenzamide. As shown in Scheme 9, hydrogen sulfide gas was bubbled into a solution of 2.75 g (7.8 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-benzonitrile in 20 mL of ethanol and triethylamine (5:4 v/v) for 10 minutes. The solution was then heated to 80° C. in a sealed pressure tube for 5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate twice. The organic extracts were washed with brine, dried (MgSO4), filtered and evaporated to give 3.0 g of crude product which was used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9307dfeacb8c439a8d57dac18a070944
Source dataset
uspto-grants-2004_03
Patent number
US06699873B1

Reaction notes

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