Dimethylcarbamoyl Chloride → HCID 15017030, compound

HRID 2050887Notes

Reaction equation

HRID 2050887 reaction equation
Br.Br.[C:3]([C:7]1[N:11]=[C:10]([S:12][CH2:13][CH2:14][NH2:15])[NH:9][N:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19].[CH2:22]([N:24]([CH2:27]C)[CH2:25]C)C.C1C[O:32]CC1>CN(C)C1C=CN=CC=1>[CH3:16][N:17]([CH3:21])[C:18]([N:9]1[C:10]([S:12][CH2:13][CH2:14][NH:15][C:22](=[O:32])[N:24]([CH3:27])[CH3:25])=[N:11][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[N:8]1)=[O:19]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178419251HCID 178419251, compound

Product 1

HCID 15017030HCID 15017030, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To 10 g (27 mmole) of 3-t-butyl-5-(2-aminoethylthio)-1H-1,2,4-triazole dihydrobromide in 50 ml of THF was added 0.5 g of 4-dimethylaminopyridine and 6 g (54 mmole) of dimethylcarbamoyl chloride and the mixture was stirred at room temperature for five minutes. Then 10 g of triethylamine was added dropwise and the mixture was refluxed for five minutes then stirred overnight at room temperature. Workup essentially as in Example 1, Step B, followed by crystallization from ether-hexane yielded 1-dimethylcarbamoyl-3-t-butyl-5-(2-(dimethylcarbamoylamino)-ethylthio)-1H-1,2,4-triazole, m.p. 82-83.

Workup

  1. temperaturethe mixture was refluxed for five minutes
  2. stirringthen stirred overnight at room temperature
  3. customWorkup essentially as in Example 1, Step B, followed by crystallization from ether-hexane

Sources & evidence

ORD record
ord-19c85dbf9065433d92732b59ce14cb8e
Source dataset
uspto-grants-1991_05
Patent number
US05015652

Reaction notes

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