Potassium Carbonate → HCID 12282017, compound

HRID 972315Notes

Reaction equation

HRID 972315 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]([NH:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([S:19]([NH2:22])(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[O:9])[C:5](=[O:23])[N:4]([CH3:24])[C:3]1=[O:25].[C:26]12([N:36]=[C:37]=[O:38])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:26]12([NH:36][C:37]([NH:22][S:19]([N:16]3[CH2:17][CH2:18][CH:13]([CH2:12][CH2:11][NH:10][C:8]([C:6]4[C:5](=[O:23])[N:4]([CH3:24])[C:3](=[O:25])[N:2]([CH3:1])[CH:7]=4)=[O:9])[CH2:14][CH2:15]3)(=[O:21])=[O:20])=[O:38])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20599951-IsocyanatoadamantaneHCID 12282041HCID 12282041, compound

Product 1

HCID 12282017HCID 12282017, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 380 mg. (0.001 mole) of 4-[2-(1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione-5-carboxamido)ethyl]-1-piperidinesulfonamide, 220 mg. (0.001 mole) of 1-adamantyl isocyanate and 310 mg. (0.002 mole) of anhydrous potassium carbonate in 30 ml. of acetone was refluxed for a period of 20 hours. At the end of this time, the spent reaction mixture was cooled and the excess potassium carbonate subsequently removed therefrom by means of suction filtration. The resulting filtrate was then slowly acidified with 1N aqueous hydrochloric acid causing a white precipitate to form. The latter material was subsequently recovered by suction filtration and thereafter recrystallized from acetonitrile-methanol to afford 220 mg (38%) of pure 1-(1-adamantyl)3-{4-[2-(1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione-5-carboxamido)ethyl]-1-piperidinesulfonyl}urea, m.p. 224°-226° C.

Workup

  1. additionA mixture of 380 mg
  2. customAt the end of this time, the spent reaction mixture
  3. temperaturewas cooled
  4. customthe excess potassium carbonate subsequently removed
  5. filtrationby means of suction filtration
  6. customto form
  7. filtrationThe latter material was subsequently recovered by suction filtration
  8. customrecrystallized from acetonitrile-methanol

Sources & evidence

ORD record
ord-e759145506ea44cd94d04ffdb456bb04
Source dataset
uspto-grants-1977_10
Patent number
US04052507

Reaction notes

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