Ethanethiol → HCID 13912578, compound

HRID 1788692Notes

Reaction equation

HRID 1788692 reaction equation
[CH2:1]([S:5]([N:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([CH3:28])[N:10]=[C:9]1[S:29]CC1C=CC(OC)=CC=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].F[C:40](F)(F)[C:41]([OH:43])=O.[CH2:46](S)C>ClCCl>[CH:2]([O:43][CH:41]([CH3:40])[CH3:46])([CH3:3])[CH3:1].[CH2:1]([S:5]([N:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([CH3:28])[NH:10][C:9]1=[S:29])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 6422Trifluoroacetic acidHCID 13912575HCID 13912575, compound

Product 2

HCID 7914Diisopropyl EtherHCID 13912578HCID 13912578, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.80 g (0.0014 mole) of 1-(Butylsulfonyl)-1, 6-dihydro-2-[[(4-methoxyphenyl) methyl]thio]-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester, 0.52 ml (0.0057 mole) of trifluoroacetic acid and 0.21 g (0.0032 mole) of ethanethiol in 15 ml of dichloromethane was stirred at room temperature for 24 hours. The solvent was evaporated, and the residue was flash chromatographed using ethyl acetate/ hexane (1:4) to give an oil which solidified very slowly. Trituration with isopropyl ether gave 0.33 g of the title compound as a colorless solid, melting point 118°-120° C. Analysis Calc'd. for C18H23N3O6S2 : C, 48.96; H, 5.25; N, 9.51; S, 14.52. Found: C, 48.99; H, 5.42; N, 9.32; S, 14.48.

Workup

  1. customThe solvent was evaporated
  2. customchromatographed
  3. customto give an oil which

Sources & evidence

ORD record
ord-0823753611834577b41a22c78ed917ba
Source dataset
uspto-grants-1987_08
Patent number
US04684656

Reaction notes

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