Dimethyl N-cyanodithioiminocarbonate → HCID 178469304, compound

HRID 464631Notes

Reaction equation

HRID 464631 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[N:8]=[N:7][C:6]([CH2:9][O:10][CH2:11][C:12]2[NH:13][C:14]([CH3:35])=[C:15]([C:31]([O:33][CH3:34])=[O:32])[CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[Cl:30])[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:5]1.[CH3:36][S:37][C:38](SC)=[N:39][C:40]#[N:41]>CC(O)C>[Cl:30][C:24]1[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH:16]1[C:15]([C:31]([O:33][CH3:34])=[O:32])=[C:14]([CH3:35])[NH:13][C:12]([CH2:11][O:10][CH2:9][C:6]2[N:7]=[N:8][N:4]([CH2:3][CH2:2][NH:1][C:38](=[N:39][C:40]#[N:41])[S:37][CH3:36])[N:5]=2)=[C:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 70042414HCID 70042414, compound

Product 1

HCID 178469304HCID 178469304, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-(2-aminoethyl)-5-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}tetrazole (1.04 g) and dimethyl N-cyanoimidodithiocarbonate (0.30 g) in propan-2-ol (10 ml) was heated under reflux for 16 hours and then evaporated. The residual oil was triturated with hexane containing a small amount of methanol and the resulting solid was collected washed with hexane and dried to give 5-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-2-[2-(3-cyano-2-methyl-1-isothioureido)ethyl]tetrazole (0.75 g), m.p. 78°-80° C. Found: C,48.53; H,4.93; N,17.60. C25H28Cl2N8O5S requires C,48.23; H,4.34; N,18.00%.

Workup

  1. temperatureunder reflux for 16 hours
  2. customevaporated
  3. customThe residual oil was triturated with hexane containing a small amount of methanol
  4. customthe resulting solid was collected
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-9171ecaf631045d1a4b889c0e584cc15
Source dataset
uspto-grants-1985_10
Patent number
US04548935

Reaction notes

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