Ethanethiol → HCID 14855104, compound

HRID 1722394Notes

Reaction equation

HRID 1722394 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21]([O:23][CH3:24])=[O:22])=[C:9]([CH3:25])[N:8]=[C:7]1[S:26]CC1C=CC(OC)=CC=1)=[O:5])[CH3:2].F[C:37](F)(F)[C:38]([OH:40])=O.[CH2:43](S)C>ClCCl>[CH:9]([O:40][CH:38]([CH3:37])[CH3:43])([CH3:25])[CH3:10].[CH2:1]([NH:3][C:4]([N:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21]([O:23][CH3:24])=[O:22])=[C:9]([CH3:25])[NH:8][C:7]1=[S:26])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 6422Trifluoroacetic acidHCID 14855103HCID 14855103, compound

Product 2

HCID 7914Diisopropyl EtherHCID 14855104HCID 14855104, compoundYield 165%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[(Ethylamino)carbonyl]-1,6-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, methyl ester (0.94 g, 1.89 mmole) in 10 ml of dry dichloromethane under argon at room temperature was treated with trifluoroacetic acid (0.5 ml, 0.74 g, 6.5 mmole) and ethanethiol (0.35 ml, 0.29 g, 4.67 mmole) and the mixture was allowed to stir overnight. Volatiles were removed in vacuo and the residue upon trituration with isopropyl ether, gave 0.59 g of the title compound, melting point 244°-246° C.

Workup

  1. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-2c854140c60e40daa33616999ac9b58a
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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