Triethylamine → HCID 20354904, compound

HRID 1606059Notes

Reaction equation

HRID 1606059 reaction equation
[CH2:1]([N:4]([CH2:8][CH:9]=[CH2:10])[C:5](Cl)=[O:6])[CH:2]=[CH2:3].[CH2:11]([S:13][C:14]1[N:18]=[CH:17][NH:16][N:15]=1)[CH3:12].C(N(CC)CC)C>O1CCCC1>[CH2:1]([N:4]([CH2:8][CH:9]=[CH2:10])[C:5]([N:16]1[CH:17]=[N:18][C:14]([S:13][CH2:11][CH3:12])=[N:15]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3449313Diallylcarbamyl chlorideHCID 178477350HCID 178477350, compound

Product 1

HCID 20354904HCID 20354904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diallylcarbamoyl chloride (8 g.) was added to a solution of 7.1 g. 3-ethylthio-1,2,4 -triazole and 8 ml. dry triethylamine in 50 ml. dry tetrahydrofuran and the mixture refluxed for 4 hours under anhydrous conditions. The cooled reaction mixture was diluted with 100 ml. toluene and washed, firstly with 1N aqueous sodium hydroxide and then with water. The resulting solution was dried over anhydrous sodium sulphate and distilled under reduced pressure to remove the solvent and give 1-diallylcarbamoyl-3-ethylthio-1,2,4-triazole, b.p. 120° - 122°C./0.1 mm. (97.1% 1-isomer by GLC assay).

Workup

  1. customThe cooled reaction mixture
  2. additionwas diluted with 100 ml
  3. washtoluene and washed, firstly with 1N aqueous sodium hydroxide
  4. dry with materialThe resulting solution was dried over anhydrous sodium sulphate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-274e7ae1264c4935840ce4cf7677273d
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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