Dimethyl N-cyanodithioiminocarbonate → HCID 178487240, compound

HRID 1788629Notes

Reaction equation

HRID 1788629 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[NH2:14])=[CH:6][CH:5]=1.[CH3:15][S:16][C:17](SC)=[N:18][C:19]#[N:20]>C(O)C>[C:19]([N:18]=[C:17]([S:16][CH3:15])[NH:14][CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1)#[N:20]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 201899077-Methoxy-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

Product 1

HCID 178487240HCID 178487240, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 17.8 g of 7-methoxy-1,2,3,4-tetrahydro-1-naphthylamine hydrochloride in 150 ml of ethanol at 0° C. was added 15.5 g of dimethyl cyanodithioiminocarbonate over a period of 30 minutes. The mixture was then allowed to remain at room temperature for 2 days after which the reaction mixture was cooled and the resulting crystals were collected by filtration. Concentration of the mother liquor gave a second crop of crystals. The combined product was recrystallized from ethanol to give 19.9 g of N'-cyano-N-(7-methoxy-1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea as colorless plates, mp 131°-132° C.

Workup

  1. temperatureafter which the reaction mixture was cooled
  2. filtrationthe resulting crystals were collected by filtration
  3. customConcentration of the mother liquor gave a second crop of crystals
  4. customThe combined product was recrystallized from ethanol

Sources & evidence

ORD record
ord-eb991366bcba4f99849aa733add047f5
Source dataset
uspto-grants-1987_08
Patent number
US04684398

Reaction notes

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