Acetone → N-(1-cyclopropylmethyl-3-pyrrolidinylmethyl)-2,3-dimethoxy-5-sulphamoyl benzamide

HRID 652781Notes

Reaction equation

HRID 652781 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:8][C:4]=1[C:5]([OH:7])=O.CC(C)=O.ClC(OCC(C)C)=O.[CH:30]1([CH2:33][N:34]2[CH2:38][CH2:37][CH:36]([CH2:39][NH2:40])[CH2:35]2)[CH2:32][CH2:31]1>O.C(N(CC)CC)C>[CH:30]1([CH2:33][N:34]2[CH2:38][CH2:37][CH:36]([CH2:39][NH:40][C:5](=[O:7])[C:4]3[CH:8]=[C:9]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:10]=[C:11]([O:12][CH3:13])[C:3]=3[O:2][CH3:1])[CH2:35]2)[CH2:31][CH2:32]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 30176982,3-Dimethoxy-5-sulphamoylbenzoic acidHCID 201968231-Cyclopropylmethyl-3-aminomethyl-pyrrolidine

Product 1

HCID 54178752N-(1-cyclopropylmethyl-3-pyrrolidinylmethyl)-2,3-dimethoxy-5-sulphamoyl benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

6.6 g of 2,3-dimethoxy-5-sulphamoyl benzoic acid, 50 ml of acetone, 10 ml of water and 3.6 ml of triethylamine (density 0.726) are placed in a 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. The solution is cooled to 0°-+5° C. and 3.6 g of isobutyl chloroformate is poured in drop by drop. It is reacted for 30 minutes with the same temperature maintained, after which 4.8 g of 1-cyclopropylmethyl-3-aminomethyl-pyrrolidine is added drop by drop. The reaction medium is agitated for 1 hour at room temperature, whereupon 50 ml of water is added and the acetone evaporated under vacuum. A further 50 ml of water is added and the solution is made alkaline with 5 ml of ammonia (density=0.91). An oil is precipitated. The suspension is extracted 3 times with 50 ml of methylene chloride. The organic phase is dried over magnesium sulphate, filtered, then evaporated under vacuum. The residue is dissolved in boiling ethyl acetate. It crystallises hot. The crystals are cooled, filtered and dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. temperatureThe solution is cooled to 0°-+5° C.
  3. customIt is reacted for 30 minutes with the same temperature
  4. temperaturemaintained
  5. additionis added
  6. customthe acetone evaporated under vacuum
  7. additionA further 50 ml of water is added
  8. customAn oil is precipitated
  9. extractionThe suspension is extracted 3 times with 50 ml of methylene chloride
  10. dry with materialThe organic phase is dried over magnesium sulphate
  11. filtrationfiltered
  12. customevaporated under vacuum
  13. dissolutionThe residue is dissolved
  14. customIt crystallises hot
  15. temperatureThe crystals are cooled
  16. filtrationfiltered
  17. customdried in an oven at 50° C.

Sources & evidence

ORD record
ord-21c47a3642c341d596ed562ff6ead4cb
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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