Methanethiol → N-(2-chlorophenylsulfonyl)-N'-(4-methoxy-6-methyl-2-pyrimidinyl) thiourea

HRID 330451

Reaction equation

HRID 330451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12](=[S:15])SC)(=[O:10])=[O:9].CS.[NH2:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([CH3:27])[N:20]=1>C1(C)C(C)=CC=CC=1.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([NH:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([CH3:27])[N:20]=1)=[S:15])(=[O:9])=[O:10]

Participants

6

Reactant 3

HCID 878MethanethiolHCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 13364655Methyl (2-chlorobenzene-1-sulfonyl)carbamodithioate

Product 1

HCID 14275697N-(2-chlorophenylsulfonyl)-N'-(4-methoxy-6-methyl-2-pyrimidinyl) thioureaYield 84.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

A solution of 5.0 g of methyl N-(2-chlorophenylsulfonyl)dithiocarbamate in 20 ml of xylene is stirred for 3.5 hours with heating at 145° C. During the heating, methylmercaptan gas is generated. After the reaction is completed, xylene is removed under reduced pressure to yield a pale yellow oil (IR: strong absorption band of -SO2NCS at 1900 cm-1). The oily substance is dissolved in 50 ml of acetonitrile, to which 2.8 g of 2-amino-4-methoxy-6-methylpyrimidine is added and stirred for 30 minutes at 50° C. The precipitated crystals are collected by filtration, and recrystallized from acetonitrile to give 5.6 g of the title compound as a white prism. mp 186.5°~187.5° C.

Workup

  1. customxylene is removed under reduced pressure
  2. customto yield a pale yellow oil (IR: strong absorption band of -SO2NCS at 1900 cm-1)
  3. additionis added
  4. filtrationThe precipitated crystals are collected by filtration
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-03289b2be8f149a7808885c2de492294
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Linked notes

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