Phosphorus oxychloride → HCID 14537090, compound

HRID 232240Notes

Reaction equation

HRID 232240 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.P(Cl)(Cl)([Cl:14])=O.[S:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>CCOCC>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4]([Cl:14])=[C:21]3[CH2:22][S:17][CH2:18][CH2:19][C:20]3=[N:1][C:2]=2[CH:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66173Tetrahydrothiopyran-4-oneHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 14537090HCID 14537090, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a slurry of 14.8 g (0.0863 mol) of 2-amino-4-chlorobenzoic acid and 150 ml of phosphorous oxychloride is added dropwise 10 g (0.086 mol) of tetrahydrothiopyran-4-one. The mixture is stirred at reflux for 3 hours and then concentrated in vacuo. The residue is dissolved in methylene chloride and edded 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 furnishes 15 g (64%) of title compound: m.p. 112°-115° C.; IR (KBr) 1605, 1480, and 1415 cm-1 ; NMR (CDCl3) δ 8.08-8.02 (m, 2H), 7.58-7.52 (m, 1H), B 4.08 (s, 2H), 3.44 (t, 2H), and 3.09 (t, 2H).

Workup

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

Sources & evidence

ORD record
ord-04ceb89a71384162b253be0b4c2590c5
Source dataset
uspto-grants-1989_07
Patent number
US04851536

Reaction notes

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