Diethylcarbamoyl chloride → HCID 19799635, compound

HRID 1886591Notes

Reaction equation

HRID 1886591 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.[CH2:29]([N:31]([CH2:35][CH3:36])[C:32](Cl)=[O:33])[CH3:30].[Cl-].[Ca+2].[Cl-]>O1CCCC1.O>[CH2:29]([N:31]([CH2:35][CH3:36])[C:32]([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:33])[CH3:30]

Participants

7

Reactant 4

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 5284359Calcium ChlorideHCID 19799580HCID 19799580, compound

Product 1

HCID 19799635HCID 19799635, compoundYield 60.1%

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, 2.5 g (0.018 mole) of diethylcarbamoyl chloride was added. After stirring an additional 15 hr, the reaction was treated with 10 ml of water and saturated with calcium chloride. The tetrahydrofuran was decanted from the solid residue and concentrated in vacuo to an oil. The crude oil was chromatographed on a Water's Prep-LC using 50% ethyl acetate/toluene as the eluent. After concentration of the main fractions 3.1 g (60.1%) of pale yellow oil was obtained.

Workup

  1. customThe tetrahydrofuran was decanted from the solid residue
  2. concentrationconcentrated in vacuo to an oil
  3. customThe crude oil was chromatographed on a Water's Prep-LC using 50% ethyl acetate/toluene as the eluent

Sources & evidence

ORD record
ord-c3d13f55307f4f71a2764e621fd8ff8f
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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