Dimethylcarbamoyl Chloride → HCID 19799571, compound

HRID 2081396Notes

Reaction equation

HRID 2081396 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:21])([F:20])[C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH:13]1[CH2:16][NH:15][CH2:14]1.C(N(CC)CC)C.[CH3:29][N:30]([CH3:34])[C:31](Cl)=[O:32].[Cl-].[Ca+2].[Cl-]>O1CCCC1.O>[CH3:29][N:30]([CH3:34])[C:31]([N:15]1[CH2:16][CH:13]([O:12][C:11]2[CH:17]=[CH:18][CH:19]=[C:9]([C:8]([F:7])([F:20])[F:21])[CH:10]=2)[CH2:14]1)=[O:32]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 5284359Calcium ChlorideHCID 19799580HCID 19799580, compound

Product 1

HCID 19799571HCID 19799571, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred slurry of 5 g (0.0163 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate in 50 ml of tetrahydrofuran was treated with 5 ml of triethylamine and after 1 hr, 1.95 g (0.018 mole) of dimethylcarbamoyl chloride was added. After stirring an additional 15 hr, the reaction mixture was treated with 20 ml of water and 10 g of calcium chloride. The tetrahydrofuran layer was decanted and the residue triturated with 20 ml of ethyl acetate, then decanted. The combined tetrahydrofuran and ethyl acetate solution was concentrated in vacuo. The crude residue was chromatographed on a Waters Prep-LC using 50% ethyl acetate/toluene as the eluent. After concentration of the main fractions, 3.6 g (76.6%) of pale yellow oil was obtained.

Workup

  1. customThe tetrahydrofuran layer was decanted
  2. customthe residue triturated with 20 ml of ethyl acetate
  3. customdecanted
  4. concentrationThe combined tetrahydrofuran and ethyl acetate solution was concentrated in vacuo
  5. customThe crude residue was chromatographed on a Waters Prep-LC

Sources & evidence

ORD record
ord-8fb63af84d464f5aaf2138ef6bd2a5f9
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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