Hydrogen Sulfide → HCID 18986141, compound

HRID 2396755Notes

Reaction equation

HRID 2396755 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[NH:11][C:12]([C:14]2[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[O:13])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:33]>C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:26])[NH:11][C:12]([C:14]2[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:8]=1)(=[S:33])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 18986137HCID 18986137, compound

Product 1

HCID 18986141HCID 18986141, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of the product of step (a) (600 mg), pyridine (56 ml) and triethylamine (8 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 stirred with dry ether for 1 hour. The resultant solid was collected and washed thoroughly with ether to give methyl 4-[4-(4-thiocarbamoylphenyl)allophanoyl]phenoxyacetate (593 mg) as a yellow solid; m.p. 215°-218° C. (decomposes); NHR Spectrum (DMSO-d6 +CD3CO2D) 3.73 (3H, s), 4.90 (2H, s), 7.08 (2H, d), 7.64 (2H, d), 7.98 (2H, d), 8.06 (2H, d); Mass Spectrum m/Z 388 (M+H)+.

Workup

  1. customThe dark green reaction mixture was evaporated to dryness
  2. stirringthe residue was stirred with dry ether for 1 hour
  3. customThe resultant solid was collected
  4. washwashed thoroughly with ether

Sources & evidence

ORD record
ord-6301b1b7ddd446779fcb2300791fc731
Source dataset
uspto-grants-1996_02
Patent number
US05494922

Reaction notes

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