Dimethylcarbamoyl Chloride → HCID 19799571, compound

HRID 1032106Notes

Reaction equation

HRID 1032106 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 Water's 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 Water's Prep-LC using 50% ethyl acetate/toluene as the eluent

Sources & evidence

ORD record
ord-0f49ca02b4584d95add228825a539603
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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