Hydrogen Sulfide → HCID 22478982, compound

HRID 736484Notes

Reaction equation

HRID 736484 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)#[N:2].CCN(CC)CC.[SH2:20]>N1C=CC=CC=1>[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[S:20])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 2708714-(Cyanomethyl)benzoic acid

Product 1

HCID 22478982HCID 22478982, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred suspension of 4-cyanomethyl-benzoic acid (1.65 g, 10.24 mmol) and Et3N (5 ml) in pyridine, H2S was bubbled during 3 h. The reaction mixture was stirred 16 h at room temperature. Water was then added to the reaction mixture which was agitated for 1 h before acidifying to pH 6 with 1M HCl. The solvent was evaporated and the residue was triturated 30 min. in water (20 ml) and filtered to obtain the title compound 250 (2.08 g, 83%) as a white solid. 1H NMR (DMSO) δ (ppm): 12.85 (bs, 1H), 9.53 (bs, 1H), 9.43 (bs, 1H), 7.88 (d, J=8.1 Hz, 2H), 7.44 (d. J=8.1 Hz, 2H), 3.88 (s, 2H).

Workup

  1. customwas bubbled during 3 h
  2. additionWater was then added to the reaction mixture which
  3. stirringwas agitated for 1 h
  4. customThe solvent was evaporated
  5. customthe residue was triturated 30 min. in water (20 ml)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f3c7ae9dfec244808e012ad09fb6c54c
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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