Dimethyl N-cyanodithioiminocarbonate → HCID 22033240, compound

HRID 1792353Notes

Reaction equation

HRID 1792353 reaction equation
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][NH2:6].[CH3:12][S:13][C:14](SC)=[N:15][C:16]#[N:17]>C(O)C>[C:16]([NH:15][C:14](=[N:6][CH2:5][CH2:4][CH2:3][C:2]([F:11])([F:1])[C:7]([F:8])([F:9])[F:10])[S:13][CH3:12])#[N:17]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 22033358HCID 22033358, compound

Product 1

HCID 22033240HCID 22033240, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4,5,5,5-pentafluoropentylamine (0.118M, 30 ml, 3.55 mmole) and of dimethyl N-cyanodithioiminocarbonate (700 mg, 4.26 mmole) in ethanol (30 ml) was heated under reflux for 18 hours. Concentration under reduced pressure, followed by crystallization from ethyl acetate and petroleum ether afforded 1-cyano-3-(4,4,5,5,5-pentafluoropentyl)-2-methylisothiourea (677 mg, 69%).

Workup

  1. temperatureunder reflux for 18 hours
  2. concentrationConcentration under reduced pressure
  3. customfollowed by crystallization from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-4810b82c804b41a28eba417fe9173a71
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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