Dimethyl N-cyanodithioiminocarbonate → HCID 178490135, compound

HRID 1004767Notes

Reaction equation

HRID 1004767 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:21])[CH2:16][NH:17][CH2:18][CH2:19][NH2:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22]([N:24]=[C:25](SC)SC)#[N:23]>C(O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:21])[CH2:16][N:17]3[CH2:18][CH2:19][NH:20][C:25]3=[N:24][C:22]#[N:23])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 18793513HCID 18793513, compound

Product 1

HCID 178490135HCID 178490135, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 22 (0.0068 mol) and dimethyl cyanocarbonimidodithioate (0.0068 mol) in ethanol (20 ml) was stirred and refluxed for 2 days. The solvent was evaporated and the residue was first purified by short open column chromatography over silica gel (eluent: CH2Cl2, CH2Cl2 /CH3OH 96/4 and 90/10), then twice by HPLC (1 eluent: CH2Cl2 /CH3OH 90/10 and 2. Eluent: CH2Cl2 /CH3OH 96/4). The pure fractions were collected and the solvent was evaporated, yielding 0.3 g (13%) of (±)-[1-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]propyl]-2-imidazolidinylidene] cyanamide (compound 1).

Workup

  1. temperaturerefluxed for 2 days
  2. customThe solvent was evaporated
  3. customthe residue was first purified by short open column chromatography over silica gel (eluent: CH2Cl2, CH2Cl2 /CH3OH 96/4 and 90/10)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-83475355836d4344b5c1e7308e4a2086
Source dataset
uspto-grants-2000_04
Patent number
US06051718

Reaction notes

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