Water → HCID 178503587, compound

HRID 2164534Notes

Reaction equation

HRID 2164534 reaction equation
Cl.[CH3:2][CH:3]([CH3:7])[C:4](=[NH:6])[NH2:5].[H-].[Na+].[C:10]([C:12](=[C:17](SC)[S:18][CH3:19])[C:13](OC)=[O:14])#[N:11].O>CN(C)C=O>[CH3:2][CH:3]([C:4]1[NH:6][C:17]([S:18][CH3:19])=[C:12]([C:10]#[N:11])[C:13](=[O:14])[N:5]=1)[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 319957Methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoateHCID 27820532-Methylpropanimidamide hydrochloride

Product 1

HCID 178503587HCID 178503587, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 2-methylpropanimidamide hydrochloride (7.0 g, described in Example 7) in dimethylformamide (15 mL) was added dropwise to a suspension of sodium hydride (3.0 g, 50% in mineral oil, prewashed with hexane) in dimethylformamide (15 mL) and the whole mixture was left at 25° C. for 1 hr. 2-Cyano-3,3-bis(methylthio)-2-propenoic acid, methyl ester (6.5 g) in dimethylformamide (15 mL) was then added dropwise, and the reaction mixture was stirred for an additional 4 hr at 25° C. Water (25 mL) was then added, and acidification with concentrated hydrochloric acid (10 mL) precipitated the product. The precipitate was collected and air dried to give the title compound (6.0 g): mp>260° C.

Workup

  1. customacidification with concentrated hydrochloric acid (10 mL) precipitated the product
  2. customThe precipitate was collected
  3. customair dried

Sources & evidence

ORD record
ord-76a9c31ad9f24d1c811245ad555a643c
Source dataset
uspto-grants-1985_03
Patent number
US04505910

Reaction notes

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