Phosphorus trichloride → HCID 12898855, compound

HRID 1659157Notes

Reaction equation

HRID 1659157 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3]1.P(Cl)(Cl)Cl.[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[CH:24][C:20]=1[C:21](O)=[O:22]>N1C=CC=CC=1>[CH:7]1([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:21](=[O:22])[C:20]3[CH:24]=[C:25]([S:28](=[O:30])(=[O:31])[NH2:29])[CH:26]=[CH:27][C:19]=3[O:18][CH3:17])[CH2:3]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 896012-Methoxy-5-sulfamoylbenzoic acidHCID 36700741-Cyclohexylpyrrolidin-3-amine

Product 1

HCID 12898855HCID 12898855, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3.7 g. (0.022 mole) of 3-amino-1-cyclohexylpyrrolidine in 100 ml. of pyridine was added dropwise with cooling 1.1 g. (0.008 mole) of phosphorous trichloride at 20°C. After stirring one hour, 3 g. (0.013 mole) of 2-methoxy-5-sulfamoylbenzoic acid was added and refluxed 6 hrs. The solution was concentrated and the residue partitioned between dilute hydrochloride acid and isopropyl ether. The acid was made basic with ammonium hydroxide and extracted with chloroform which was dried (sodium sulfate) and concentrated. The residue was crystallized from ethyl acetate and recrystallized from isopropyl alcohol. Yield 1 g. (33%); m.p. 184°-187°C.

Workup

  1. temperaturewith cooling 1.1 g
  2. customat 20°C
  3. temperaturerefluxed 6 hrs
  4. concentrationThe solution was concentrated
  5. customthe residue partitioned between dilute hydrochloride acid and isopropyl ether
  6. extractionextracted with chloroform which
  7. dry with materialwas dried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe residue was crystallized from ethyl acetate
  10. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-1a27a56fd18e4f9ca919faf608818a34
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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