Dimethylcarbamoyl Chloride → HCID 14856776, compound

HRID 1073533Notes

Reaction equation

HRID 1073533 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([S:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][O:13]2)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:17][N:18]([CH3:22])[C:19]([N:7]1[C:8]([S:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[N:9][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6]1)=[O:20]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178441981HCID 178441981, compound

Product 1

HCID 14856776HCID 14856776, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-t-Butyl-5-(1,3-dioxolan-2-yl-methylthio)-1H-1,2,4-triazole (7 g, 28.8 mmole), 2.8 ml (30.5 mmole) of dimethylcarbamoyl chloride, 8 ml (57 mmole) of triethylamine and 0.5 g (4.1 mmole) of 4-dimethylaminopyridine were dissolved in 50 ml of tetrahydrofuran (THF). The mixture was refluxed for four hours, concentrated in vacuo and partitioned between methylene chloride and dilute hydrochloric acid. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Chromatography on silica gel using ethyl ether/hexane gave 1-dimethylcarbamoyl-3-t-butyl-5-(1,3-dioxolan-2-yl-methylthio)-1H-1,2,4triazole, an oil.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. concentrationconcentrated in vacuo
  3. custompartitioned between methylene chloride and dilute hydrochloric acid
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c859ac1af2be4079a5d9fe36b3cf1a79
Source dataset
uspto-grants-1990_11
Patent number
US04970224

Reaction notes

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