Potassium Carbonate → HCID 20504611, compound

HRID 1701970Notes

Reaction equation

HRID 1701970 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]([NH:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=S)(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[O:9])[C:4](=[O:32])[CH2:3]1.CC1CCN(C(NCCC2C=CC(S(N)(=O)=O)=CC=2)=[O:41])C(=O)C1.C1(N=C=O)CCCCC1.C(=O)([O-])[O-].[K+].[K+].N([O-])=O.[Na+]>CC(C)=O.O.C(O)(=O)C>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]([NH:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:41])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[O:9])[C:4](=[O:32])[CH2:3]1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 18502Cyclohexyl isocyanateHCID 20504601HCID 20504601, compoundHCID 20504610HCID 20504610, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20504611HCID 20504611, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

1.2 g N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl-thio-urea (m.p. 179°-181° C., prepared from 4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonamide and cyclohexyl-isocyanate in acetone in the presence of potassium carbonate) are dissolved in 75 ml of acetone and 10 ml of water. At 0° C., a solution of 0.1 g of sodium nitrite in 5 ml of water is added to this solution, subsequently 0.8 ml of 5 N acetic acid is added dropwise, and agitation is continued for 2 hours at 0° C. Subsequently, the acetone is evaporated under reduced pressure, the product is suction-filtered and reprecipitated from dilute ammonia. After recrystallization from dilute acetone, N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea has a melting point of 176°-178° C., and with the product prepared according to Example 8, shows no depression.

Workup

  1. additionis added dropwise
  2. customSubsequently, the acetone is evaporated under reduced pressure
  3. filtrationthe product is suction-filtered
  4. customreprecipitated from dilute ammonia
  5. customAfter recrystallization from dilute acetone, N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea
  6. customwith the product prepared

Sources & evidence

ORD record
ord-316cc090158345e089273f5a6e3bcfd3
Source dataset
uspto-grants-1983_04
Patent number
US04379785

Reaction notes

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