Hydrogen Sulfide → HCID 19610525, compound

HRID 977026Notes

Reaction equation

HRID 977026 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-3979a8524c014e7c9dd877dad85d986c
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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