Phosgene → HCID 20504611, compound

HRID 1701972Notes

Reaction equation

HRID 1701972 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].[CH3:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32](Cl)=[O:33])[C:28](=[O:35])[CH2:27]1.[Na].CC1CCNC(=O)C1.C(Cl)(Cl)=O>O.CC(C)=O>[CH3:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=2)=[O:33])[C:28](=[O:35])[CH2:27]1

Participants

9

Reactant 6

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 127955274-(2-Aminoethyl)-N-(cyclohexylcarbamoyl)benzene-1-sulfonamideHCID 141468784-Methylpiperidin-2-oneHCID 54018391HCID 54018391, compound

Product 1

HCID 20504611HCID 20504611, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

1.6 g of N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea and 0.2 g of sodium hydroxide are dissolved in 10 ml of water and 50 ml of acetone. With agitation and ice cooling, a solution of 0.85 g of 4-methyl-2-oxo-piperidine-1-carboxylic acid chloride (prepared by reaction of the sodium compound of 4-methyl-2-oxo-piperidine with phosgene) in 20 ml of acetone is added dropwise to this solution, and agitation is continued for 2 hours at room temperature. Subsequently, the acetone is evaporated under reduced pressure, the batch is acidified, suction-filtered, the product is reprecipitated from dilute ammonia and recrystallized from dilute acetone. The N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea obtained has a melting point of 177°-178° C. and is identical with the product obtained according to Example 8.

Workup

  1. additionis added dropwise to this solution, and agitation
  2. customSubsequently, the acetone is evaporated under reduced pressure
  3. filtrationsuction-filtered
  4. customthe product is reprecipitated from dilute ammonia
  5. customrecrystallized from dilute acetone

Sources & evidence

ORD record
ord-fedf82b360404700adffd8eb0cb6c93b
Source dataset
uspto-grants-1983_04
Patent number
US04379785

Reaction notes

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