Hydrochloric Acid → Glisindamide

HRID 894097Notes

Reaction equation

HRID 894097 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[O:12].ClC(Cl)(Cl)[C:28]([N-:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:29].C(=O)([O-])[O-].[K+].[K+].Cl>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25][C:28]([NH:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:29])(=[O:23])=[O:24])=[CH:20][CH:21]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21162331HCID 21162331, compoundHCID 178521935HCID 178521935, compound

Product 1

HCID 3038458Glisindamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

3.6 g of 4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfon-amide are carefully mixed with 2.5 g of trichloroacetyl-cyclohexyl amide and 2.8 g of potassium carbonate and the mixture is heated in a bath for 1 hour at 160° C. After cooling, the reaction mixture is treated with water and hydrochloric acid, filtered off with suction and the reaction product is reprecipitated from very dilute ammonia and recrystallized from dilute acetone. The N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl-urea obtained melts at 214°-216° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered off with suction
  3. customthe reaction product is reprecipitated from very dilute ammonia
  4. customrecrystallized from dilute acetone

Sources & evidence

ORD record
ord-c11ac8e675974bafb761175c8e531b7a
Source dataset
uspto-grants-1981_08
Patent number
US04282239

Reaction notes

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