Phosphorus oxychloride → HCID 18172454, compound

HRID 397044Notes

Reaction equation

HRID 397044 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=O)[CH:6]=[CH:7][CH:8]=1.O=P(Cl)(Cl)Cl>>[CH:14]1([C:12]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:9][CH2:10][N:11]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 47041879HCID 47041879, compound

Product 1

HCID 18172454HCID 18172454, compoundYield 93%

Procedure

A solution of cyclohexanecarboxylic acid [2-(3-methoxyphenyl)ethyl]amide (1.000 g, 3.8 mmol) in POCl3 (7.0 ml, 75.1 mmol) was refluxed under N2 for 24 hr, then the cooled reaction mixture was slowly added to ice-water (30 ml) with stirring. The resulting mixture was extracted with EtOAc (3×20 ml), then the remaining aqueous layer was basified to pH 10 with concentrated ammonia (40 ml). This was extracted with CHCl3 (4×20 ml), then the combined extracts were dried over MgSO4 and concentrated in vacuo to give 0.270 g (93% yield) of yellow oil.

Workup

  1. customthe cooled reaction mixture
  2. extractionThe resulting mixture was extracted with EtOAc (3×20 ml)
  3. extractionThis was extracted with CHCl3 (4×20 ml)
  4. dry with materialthe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7998d0ef68dc4e4cbe252a385d289ff9
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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