1,1-Bis(methylthio)-2-nitroethylene → 1-(2-Methyl-5-thiazolylmethyl)2-(nitromethylene)tetrahydropyrimidine

HRID 2211032Notes

Reaction equation

HRID 2211032 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:5][N:6]=1.[N+:13]([CH:16]=[C:17](SC)SC)([O-:15])=[O:14]>C(#N)C>[CH3:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][NH:12][C:17]2=[CH:16][N+:13]([O-:15])=[O:14])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 14009896N-(2-Methyl-5-thiazolylmethyl]trimethylenediamine

Product 1

HCID 702491131-(2-Methyl-5-thiazolylmethyl)2-(nitromethylene)tetrahydropyrimidineYield 40.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-Methyl-5-thiazolylmethyl]trimethylenediamine (18.5 g) was dissolved in 100 ml of acetonitrile, and 1-nitro-2,2-bis(methylthio)ethylene (16.5 g) was added. With stirring, the mixture was refluxed for 6 hours. After the reaction, the reaction mixture was cooled to room temperature. The resulting crystals were collected by filtration and washed with methanol to give 10.2 g of the desired 1-(2-methyl-5-thiazolylmethyl)2-(nitromethylene)tetrahydropyrimidine. mp. 204°-207° C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter the reaction
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with methanol

Sources & evidence

ORD record
ord-57aa6e37a3a6463c991d6908637c55e1
Source dataset
uspto-grants-1995_10
Patent number
US05461167

Reaction notes

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