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Dimethylcarbamoyl Chloride → 1-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(2-cyanopyridin-4-yl)benzoyl]piperazine

HRID 352919
Notes
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Reaction equation

HRID 352919 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][N+:32]([O-])=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH3:36][N:37](C)C(Cl)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:22])[C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([C:36]#[N:37])[CH:30]=4)=[CH:25][CH:24]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 516892Sodium BicarbonateHCID 226280974-[4-(4-(6-Chloronaphthalene-2-sulfonyl)piperazine-1-carbonyl)phenyl]pyridine 1-oxide

Product 1

HCID 227100851-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(2-cyanopyridin-4-yl)benzoyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

In dichloromethane (100 ml), 4-[4-[[4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]phenyl]pyridine N-oxide (1.67 g) was dissolved, followed by the addition of trimethylsilycynanide (0.42 ml) and dimethylcarbamoyl chloride (0.30 ml). The resulting mixture was stirred at room temperature for 24 hours. An aqueous solution of sodium bicarbonate and dichloromethane were added to the reaction mixture to separate the organic layer. The organic layer thus obtained was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (1% methanol—dichloromethane), whereby the title compound (1.44 g, 84%) was obtained.

Workup

  1. customto separate the organic layer
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. customwas purified by chromatography on a silica gel column (1% methanol—dichloromethane), whereby the title compound (1.44 g, 84%)
  7. customwas obtained

Sources & evidence

ORD record
ord-86631bdbb093414b900fc7773ed47957
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes