Dimethyl N-cyanodithioiminocarbonate → HCID 178497930, compound

HRID 1069163Notes

Reaction equation

HRID 1069163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:12][S:13][C:14](SC)=[N:15][C:16]#[N:17]>N1C=CC=CC=1>[C:16]([N:15]=[C:14]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[S:13][CH3:12])#[N:17]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 178497930HCID 178497930, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of methyl 3-aminobenzoate (6.04 g, 40 mmol) and dimethyl N-cyanodithioiminocarbonate (11.96 g, 80 mmol) in pyridine (70 mL) was heated at reflux for 2.5 hours. The reaction mixture was cooled to room temperature and upon standing overnight at room temperature the above compound (6.2 g) crystallized from the reaction mixture. The compound was used without further purification. 1H NMR was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customthe above compound (6.2 g) crystallized from the reaction mixture
  4. customThe compound was used without further purification

Sources & evidence

ORD record
ord-fe885b99dfec418da6ba03171b6501f4
Source dataset
uspto-grants-2001_06
Patent number
US06251944B1

Reaction notes

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