Dimethylcarbamoyl Chloride → HCID 58758139, compound

HRID 1514031Notes

Reaction equation

HRID 1514031 reaction equation
[CH3:1][CH:2]([C:4]([CH3:9])([OH:8])[CH:5]([CH3:7])[CH3:6])[CH3:3].[H-].[Na+].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[O:15]>C1(C)C=CC=CC=1.CC(OC)(C)C>[CH:2]([C:4]([O:8][C:14](=[O:15])[N:13]([CH3:17])[CH3:12])([CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 5204842,3,4-Trimethyl-3-pentanol

Product 1

HCID 58758139HCID 58758139, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2,3,4-Trimethyl-pentan-3-ol (13.0 g, 100 mmol, 1 equiv.) in toluene (50 ml) was added to a suspension of NaH (55% in mineral oil, 4.80 g, 110 mmol, 1.1 equiv.) in toluene (50 ml). The mixture was heated to 100° C. for 1 h, then cooled to 0° C. A solution of dimethyl carbamoyl chloride (12.9 g, 120 mmol, 1.2 equiv.) in toluene (30 ml) was added over 45 min. The resulting suspension was stirred at room temperature for 19 h, then diluted with MTBE and worked up as describe in Example 1. Distillation of the crude at 0.05 mbar/52-61° C. yielded 61% of product.

Workup

  1. temperaturecooled to 0° C
  2. distillationDistillation of the crude at 0.05 mbar/52-61° C.

Sources & evidence

ORD record
ord-5b20d73ba67445729f11eb538829c952
Source dataset
uspto-grants-2012_07
Patent number
US08222200B2

Reaction notes

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