Triethylamine → 5-(Butylsulfanyl)-N-methyl-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamide

HRID 1833822Notes

Reaction equation

HRID 1833822 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].[OH:12][C:13]1[N:17]=[C:16]([S:18][CH2:19][CH2:20][CH2:21][CH3:22])[S:15][N:14]=1>C(OC(C)C)(C)C>[CH3:8][NH:9][C:10]([N:14]1[C:13](=[O:12])[N:17]=[C:16]([S:18][CH2:19][CH2:20][CH2:21][CH3:22])[S:15]1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 178454959HCID 178454959, compound

Product 1

HCID 213874895-(Butylsulfanyl)-N-methyl-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

0.5 ml of triethylamine and 4.78 g of methyl isocyanate were added to a solution of 95 g of 3-hydroxy-5-n-butylthio-1,2,4-thiadiazole in 50 ml of isopropyl ether and the mixture was stirred for 2 hours at 20° C and was vacuum filtered. The recovered precipitate was washed with isopropyl ether and dried to obtain 11.2 g of 2-(N-methylcarbamoyl)-5-n-butylthio-1,2,4-thiadiazole-3-one melting at 102° C.

Workup

  1. filtrationfiltered
  2. washThe recovered precipitate was washed with isopropyl ether
  3. customdried

Sources & evidence

ORD record
ord-f97d0883a7c24a7cb17a838a1d1a94ee
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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