Pyridine → HCID 54251428, compound

HRID 328473Notes

Reaction equation

HRID 328473 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].N1C=CC=CC=1.[CH3:13][N:14]([CH3:22])[C:15](=[O:21])[NH:16][C:17](=[NH:20])[S:18][CH3:19]>C(Cl)Cl>[CH3:1][N:2]([CH3:6])[C:3]([N:20]=[C:17]([S:18][CH3:19])[NH:16][C:15]([N:14]([CH3:22])[CH3:13])=[O:21])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 150009409HCID 150009409, compound

Product 1

HCID 54251428HCID 54251428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

5.4 Parts of dimethylcarbamoyl chloride is combined with 10 parts pyridine and stirred until the temperature returns to 25° C. 8.0 Parts methyl 4,4-dimethylthioallophanimidate (a compound of formula II), in 50 parts methylene chloride is added in one portion. The mixture is refluxed overnight, then cooled to give a white solid. The solid is removed and the organic layer is extracted with 200 parts water at pH 3, dried and evaporated to give 5 parts methyl N-dimethylcarbamoyl-4,4-dimethylthioallophanimidate (a compound of formula I), m.p. 115.5°-117.5° C.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. temperaturecooled
  3. customto give a white solid
  4. customThe solid is removed
  5. extractionthe organic layer is extracted with 200 parts water at pH 3
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-e454e5284e9e4bdf8de5ff3bbff47792
Source dataset
uspto-grants-1977_04
Patent number
US04017529

Reaction notes

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