Hydrogen Sulfide → HCID 19610525, compound

HRID 1602724Notes

Reaction equation

HRID 1602724 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][NH:10][C:11]([C:13]2[CH:24]=[CH:23][C:16]([O:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[O:12])=[O:8])=[CH:5][CH:4]=1)#[N:2].[SH2:27]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][NH:10][C:11]([C:13]2[CH:24]=[CH:23][C:16]([O:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[O:12])=[O:8])=[CH:5][CH:4]=1)(=[S:27])[NH2:2]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 19610522HCID 19610522, compound

Product 1

HCID 19610525HCID 19610525, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A solution of the product of step (b) (10 g) in a mixture of pyridine (500 ml) and triethylamine (80 ml) was covered with a blanket of H2S gas and stirred at ambient temperature overnight. The dark green reaction mixture was evaporated to dryness and the residue was triturated with dry ether. The resultant solid was collected and washed thoroughly with ether to give methyl 4-[3-(4-thiocarbamoylbenzoyl)carbazoyl]phenoxyacetate (10.5 g) as a yellow solid; NMR Spectrum (DMSO-d6) 3.72 (3H, s), 4.90 (2H, s), 7.06 (2H, d), 7.90 (2H, d), 7.95 (4H, m), 9.62 (1H, br s), 10.01 (1H, br s), 10.40 (1H, br s), 10.55 (1H, br s); Mass Spectrum m/Z 388 (M+H)+.

Workup

  1. customThe dark green reaction mixture was evaporated to dryness
  2. customthe residue was triturated with dry ether
  3. customThe resultant solid was collected
  4. washwashed thoroughly with ether

Sources & evidence

ORD record
ord-5721d5f49b4645b1aa5aaafbf637968e
Source dataset
uspto-grants-1999_11
Patent number
US05981531

Reaction notes

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