Hydrogen Sulfide → Methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate

HRID 1900874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900874
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10](=[O:24])[NH:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)=[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:4]=[CH:5][C:6]([C:7]([NH:9][C:10](=[O:24])[NH:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)=[O:8])=[CH:25][CH:26]=1)(=[S:27])[NH2:2]

Komponenten

5

Edukt 2

HCID 402Hydrogen SulfideHCID 23370013Methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate

Produkt 1

HCID 23369995Methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of the product of step (a) (850 mg) in pyridine (48 ml) and triethylamine (7 ml) was covered with a blanket of H2S gas and stirred at ambient temperature for 16 hours. The reaction mixture was evaporated to dryness and the residue was triturated with dry ether. The resultant solid was washed thoroughly with ether to give methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (880 mg) as a yellow solid: NMR Spectrum (DMSO-d6) 3.72 (3H, s), 4.78 (2H, s), 6.95 (2H, d), 7.48 (2H, m), 7.93 (2H, d), 8.06 (2H, d), 9.65 (1H, br s), 10.05 (1H, br s), 10.62 (1H, s).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was triturated with dry ether
  3. washThe resultant solid was washed thoroughly with ether

Quellen und Nachweise

ORD-Eintrag
ord-b5693b3bd2404933abe9b36681371d2f
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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