Hydrochloric Acid → HCID 67855880, compound

HRID 1657033Notes

Reaction equation

HRID 1657033 reaction equation
[CH3:1][S:2][C:3](=[N:6][N+:7]([O-:9])=[O:8])[NH:4][CH3:5].CC#N.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>N1C=CC=CC=1>[C:13]([N:4]([CH3:5])[C:3](=[N:6][N+:7]([O-:9])=[O:8])[S:2][CH3:1])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 7412Benzoyl chloride2×HCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 67855880HCID 67855880, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of S,N-dimethyl-N'-nitroisothiourea (0.5 g), CH3CN (6 ml) and pyridine (1 ml) was cooled to 0° C. To the cooled mixture was added benzoyl chloride (1 g) dropwise in 5 minutes under stirring. After stirring at the same temperature for 1 hour, benzoyl chloride (0.4 g) was added to the mixture which was stirred at room temperature for 1 hour. The reaction mixture was poured into 50 ml of 2N hydrochloric acid and the resulting mixture was extracted with CHCl3. The extract was dried over MgSO4 and evaporated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (5:1) to afford 0.71 g of crude N-benzoyl-S,N-dimethyl-N'-nitroisothiourea as an oil. To the solution of the product (0.636 g) in CH3CN (4 ml) was added a solution of 2-chloro-5-thiazolylmethylamine (0.37 g) in CH3CN (2 ml) dropwise at 0° C. over 5 minutes. After stirring at the same temperature for 25 minutes, precipitates were collected by filtration and the product was applied to column chromatography on silica gel. The column was eluted with CH2Cl2 -MeOH (20:1) to afford 0.344 g of 1-benzoyl-3-(2-chloro-5-thiazolylmethyl)-l-methyl-2-nitroguanidine (Compound No. 15) as a crystal, m.p. 170°-172° C.

Workup

  1. stirringAfter stirring at the same temperature for 1 hour
  2. stirringwas stirred at room temperature for 1 hour
  3. extractionthe resulting mixture was extracted with CHCl3
  4. dry with materialThe extract was dried over MgSO4
  5. customevaporated in vacuo
  6. washThe column was eluted with hexane-AcOEt (5:1)

Sources & evidence

ORD record
ord-b9cff700b8ef4b2d821feca449b22713
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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