Dimethylcarbamoyl Chloride → HCID 86737552, compound

HRID 127212Notes

Reaction equation

HRID 127212 reaction equation
[N:1](=[C:3]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:10])([CH3:9])[S:4]1)[OH:2].C(N(CC)CC)C.[CH3:18][N:19]([CH3:23])[C:20](Cl)=[O:21]>COCCOC>[CH3:18][N:19]([CH3:23])[C:20]([O:2][N:1]=[C:3]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:10])([CH3:9])[S:4]1)=[O:21]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 859972442-Oxo-4,5,5-trimethyl-3-thiazoline oxime

Product 1

HCID 86737552HCID 86737552, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

15.8 g. (0.1 mol) of 2-oxo-4,5,5-trimethyl-3-thiazoline-oxime and 15.2 g. (0.15 mol) of triethylamine were dissolved in 100 ml. of anhydrous 1,2-dimethoxy-ethane. 16.1 g. (0.15 mol) of dimethylcarbamoyl chloride were added dropwise. The mixture was refluxed for 3 hours and the solvent was distilled off under vacuum. The residue was dissolved in 100 ml. of dichloromethane and washed with water. After the organic phase was dried over sodium sulfate, the solvent was distilled off. The residue was purified chromatographically on silica gel using ether/dichloromethane (9:1) for the elution to yield 2-oxo-4,5,5-trimethyl-3-thiazoline-O-(dimethylcarbamoyl)-oxime, m.p. 108°-110° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. distillationthe solvent was distilled off under vacuum
  3. dissolutionThe residue was dissolved in 100 ml
  4. washof dichloromethane and washed with water
  5. dry with materialAfter the organic phase was dried over sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified chromatographically on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-e28039f226eb434b8511f35135413bdf
Source dataset
uspto-grants-1981_03
Patent number
US04255436

Reaction notes

Loading…