Acetone → HCID 20196839, compound

HRID 652782Notes

Reaction equation

HRID 652782 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([CH2:36][N:37]2[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>O.C(N(CC)CC)C>[CH:30]1([CH2:36][N:37]2[CH2:41][CH2:40][CH:39]([NH:42][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])[CH2:38]2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 30176982,3-Dimethoxy-5-sulphamoylbenzoic acidHCID 218906401-(Cyclohexylmethyl)pyrrolidin-3-amine

Product 1

HCID 20196839HCID 20196839, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

7.85 g of 2,3-dimethoxy-5-sulphamoyl benzoic acid, 50 ml of acetone, 10 ml of water and 3 g of triethylamine are placed in a 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. The mixture is cooled to 0° and 4.2 g of isobutyl chloroformate is poured in drop by drop. The mixture is agitated for 45 minutes at 0° C., after which 6 g of 1-cyclohexylmethyl-3-amino-pyrrolidine is dripped in. It is agitated for 2 hours at room temperature, then 80 ml of water is added and the acetone evaporated under vacuum. The product crystallises. It is filtered, washed with water then re-dissolved in 150 ml of water and 20 ml of hydrochloric acid. The solution is filtered with charcoal and the filtrate made alkaline with ammonia. An oil is precipitated and crystallises slowly. The crystals are drained, washed with water and dried in an oven at 50° C. 6.8 g (53%) of product is obtained, with a melting point of 167° C.

Workup

  1. customfitted with an agitator
  2. temperatureThe mixture is cooled to 0°
  3. stirringIt is agitated for 2 hours at room temperature
  4. customthe acetone evaporated under vacuum
  5. customThe product crystallises
  6. filtrationIt is filtered
  7. washwashed with water
  8. dissolutionthen re-dissolved in 150 ml of water
  9. filtrationThe solution is filtered with charcoal
  10. customAn oil is precipitated
  11. customcrystallises slowly
  12. washwashed with water
  13. customdried in an oven at 50° C

Sources & evidence

ORD record
ord-f66148cd24c24ee390b1d08d985717ed
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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