Hydrochloric Acid → HCID 53822792, compound

HRID 1657027Notes

Reaction equation

HRID 1657027 reaction equation
[CH3:1][S:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].CC#N.[CH2:12]([S:15](Cl)(=[O:17])=[O:16])[CH2:13][CH3:14].Cl>O.CCN(CC)CC>[CH3:1][S:2][C:3](=[N:8][S:15]([CH2:12][CH2:13][CH3:14])(=[O:17])=[O:16])[NH:4][N+:5]([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 662791-Propanesulfonyl chlorideHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 53822792HCID 53822792, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of S-methyl-N-nitroisothiourea (5.0 g), CH3CN (50 ml) and Et3N (11.2 g) was cooled with iced water. To the cooled mixture was added 10.6 g of n-propanesulfonyl chloride dropwise below 15° C. under stirring. After stirring at the same temperature for 1 hour, the mixture was poured into a mixed solution of conc. hydrochloric acid (20 ml) and water (180 ml) and the resulting mixture was extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo to afford 9.9 g of crude crystals. Recrystallization of the product from CCl4 (5 ml) gave 5.4 g of S-methyl-N-nitro-N'-(n-propanesulfonyl)isothiourea as a pale yellow crystal, m.p. 91°-93° C.

Workup

  1. stirringAfter stirring at the same temperature for 1 hour
  2. extractionthe resulting mixture was extracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto afford 9.9 g of crude crystals
  6. customRecrystallization of the product from CCl4 (5 ml)

Sources & evidence

ORD record
ord-f698fffb73f248b3ada9feab17a7c6d8
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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