Acetone → HCID 86741589, compound

HRID 1194750Notes

Reaction equation

HRID 1194750 reaction equation
[CH3:1][O:2][CH:3]1[C:11](=[S:12](=[O:14])=[O:13])[C:10]([NH2:15])=[C:9]([CH2:16][CH3:17])[CH:8]=[C:4]1[C:5]([OH:7])=O.[CH3:18]C(C)=O.ClC(OCC)=O.[CH:28]1([N:35]2[CH2:39][CH2:38][CH2:37][C:36]2(C)[CH2:40][NH2:41])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>O.Cl.C(N(CC)CC)C>[CH:28]1([N:35]2[CH2:39][CH2:38][CH2:37][CH:36]2[CH:40]([CH3:18])[NH:41][C:5](=[O:7])[C:4]2[CH:3]([O:2][CH3:1])[C:11](=[S:12](=[O:14])=[O:13])[C:10]([NH2:15])=[C:9]([CH2:16][CH3:17])[CH:8]=2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

8

Reactant 4

HCID 180AcetoneHCID 10928Ethyl chloroformateHCID 54502136HCID 54502136, compoundHCID 86681511HCID 86681511, compound

Product 1

HCID 86741589HCID 86741589, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

4.9 g of 2methoxy-4-amino-5-ethyl sulphonyl benzoic acid, 57 ml of acetone, 10 ml of water and 2.6 ml of triethylamine (density 0.726) are placed in a 250 ml flask fitted with an agitator, a thermometer, a condenser and a dropping funnel. The solution is cooled to between 0° and +5° C. and 2.1 g of ethyl chloroformate is added drop by drop. The reaction medium is agitated for 45 minutes at room temperature then cooled to 0° C. and 5.3 g of 1-cycloheptyl methyl-2-amino methyl pyrrolidine is poured in drop by drop. The medium is agitated for 4 hours then left to stand overnight. The solvents are evaported to dryness and the residue is dissolved in 60 ml of water and 15 ml of hydrochloric acid (density 1.18). Extraction is carried out 3 times with 50 ml of methylene chloride, the organic phase is dried over magnesium sulphate and filtered, and the solvent is evaporated under vacuum. The residue is dissolved in 100 ml of water. The solution is filtered in the presence of carbon black and the filtrate is made alkaline with about 7 ml of ammonia (density 0.91). A gum is precipitated. It is extracted 3 times with 50 ml of methylene chloride. The organic phase is washed twice with 50 ml of water, dried over magnesium sulphate and filtered. The solvent is evaporated under vacuum and the residue is re-crystallized in 100 ml of isopropanol.

Workup

  1. customfitted with an agitator
  2. temperatureThe solution is cooled to between 0° and +5° C.
  3. temperaturethen cooled to 0° C.
  4. stirringThe medium is agitated for 4 hours
  5. waitthen left
  6. waitto stand overnight
  7. extractionExtraction
  8. dry with materialthe organic phase is dried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent is evaporated under vacuum
  11. dissolutionThe residue is dissolved in 100 ml of water
  12. filtrationThe solution is filtered in the presence of carbon black
  13. customA gum is precipitated
  14. extractionIt is extracted 3 times with 50 ml of methylene chloride
  15. washThe organic phase is washed twice with 50 ml of water
  16. dry with materialdried over magnesium sulphate
  17. filtrationfiltered
  18. customThe solvent is evaporated under vacuum
  19. customthe residue is re-crystallized in 100 ml of isopropanol

Sources & evidence

ORD record
ord-b649213818be4cda8e24e253e40f9a4d
Source dataset
uspto-grants-1989_03
Patent number
US04816471

Reaction notes

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