Dimethyl N-cyanodithioiminocarbonate → HCID 86608259, compound

HRID 2233878Notes

Reaction equation

HRID 2233878 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:10].[C:18]([N:20]=[C:21](SC)[S:22][CH3:23])#[N:19]>ClC(Cl)C>[C:18]([N:20]=[C:21]([N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:9]([C:3]2[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=2[Cl:1])=[O:10])[CH2:13][CH2:14]1)[S:22][CH3:23])#[N:19]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 11514618HCID 11514618, compound2×

Product 1

HCID 86608259HCID 86608259, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide (Intermediate 90, 2.73 g, 10 mmol) and dimethyl cyanodithioimidocarbonate (1.61 g, 10 mmol) in dichloroethane was heated to reflux for 5 hours. The reaction mixture was concentrated to an orange oil which was purified by flash chromatography on silica gel (gradient elution from 100% DCM to 5% MeOH in DCM). Pure fractions were combined to yield the title compound in 2.25 g (61%).

Workup

  1. temperatureto reflux for 5 hours
  2. concentrationThe reaction mixture was concentrated to an orange oil which
  3. customwas purified by flash chromatography on silica gel (gradient elution from 100% DCM to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-59469c32855944d8920d5866590f7e0b
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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