Phosphorus oxychloride → HCID 131716014, compound

HRID 232241Notes

Reaction equation

HRID 232241 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].P(Cl)(Cl)([Cl:14])=O.[C:17]1([CH:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC>[OH2:5].[Cl:11][C:9]1[CH:10]=[C:2]2[C:3](=[CH:7][CH:8]=1)[C:4]([Cl:14])=[C:25]1[C:26]([CH2:27][CH2:28][CH:23]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:24]1)=[N:1]2.[Cl:11][C:9]1[CH:10]=[C:2]2[C:3](=[CH:7][CH:8]=1)[C:4]([Cl:14])=[C:25]1[C:26]([CH2:27][CH2:28][CH:23]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:24]1)=[N:1]2

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 666462-Amino-4-chlorobenzoic acidHCID 786054-Phenylcyclohexanone

Product 1

HCID 131716014HCID 131716014, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a slurry of 15 g (0.0874 mol) of 2-amino-4-chlorobenzoic acid and 150 ml of phosphorous oxychloride is added dropwise 15 g (0.0871 mol) of 4-phenylcyclohexanone. The mixture is stirred at reflux for 3 hours and then concentrated in vacuo. The residue is dissolved in methylene chloride and added slowly to an ice-NH4OH mixture. The mixture is stirred for 1/2 hour and extracted with methylene chloride. The combined extracts are washed with water, dried over Na2SO4, and concentrated in vacuo to yield a dark solid. Trituration with ether provides 20 g (70%) of title compound: m.p. 134°-136° C.; IR 1605, 1585 and 1480 cm-1 ; NMR (CDCl3) δ 8.12-8.0 (m, 2H), 7.54-7.46 (m, 1H), 7.44-7.26 (m, 5H), 3.50-2.88 (m, 5H), and 2.28-2.02 (m, 2H).

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in methylene chloride
  4. additionadded slowly to an ice-NH4OH mixture
  5. stirringThe mixture is stirred for 1/2 hour
  6. extractionextracted with methylene chloride
  7. washThe combined extracts are washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto yield a dark solid

Sources & evidence

ORD record
ord-5da282381d214097b5661a5a98e0c4d3
Source dataset
uspto-grants-1989_07
Patent number
US04851536

Reaction notes

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