Diethylcarbamoyl chloride → HCID 19799635, compound

HRID 974557Notes

Reaction equation

HRID 974557 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 tetrahydrofruan 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 tetrahydrofruan 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-13c68b6100a949788e7eb142ba05e1f1
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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