Tetrahydrofuran → HCID 20355131, compound

HRID 371562Notes

Reaction equation

HRID 371562 reaction equation
[CH2:1]([S:6][C:7]1[N:11]=[CH:10][NH:9][N:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:12]([N:15]([CH2:19][CH:20]=[CH2:21])[C:16](Cl)=[O:17])[CH:13]=[CH2:14].O1CCCC1.C(N(CC)CC)C>CCOCC>[CH2:12]([N:15]([CH2:19][CH:20]=[CH2:21])[C:16]([N:9]1[CH:10]=[N:11][C:7]([S:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[N:8]1)=[O:17])[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 3449313Diallylcarbamyl chlorideHCID 178447699HCID 178447699, compound

Product 1

HCID 20355131HCID 20355131, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 9.5 g. 3-n-pentylthio-1,2,4-triazole, 8.07 g. diallylcarbamoyl chloride, 100 ml. dry tetrahydrofuran and 8 ml. dry triethylamine was refluxed under anhydrous conditions for 68 hours. The reaction mixture was worked up as described in Example 1, using ether in place of methylene dichloride, to produce an oil which was distilled under reduced pressure to give 1-diallylcarbamoyl-3-n-pentylthio-1,2,4-triazole, b.p. 135° C./0.1 mm. (90.6% 1-isomer by GLC assay). Elemental analysis satisfactory.

Workup

  1. additionA mixture of 9.5 g
  2. customto produce an oil which
  3. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-6a62ef3386ec4d85a4908d652871bd62
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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