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Methyl Isobutyl Ketone → HCID 21500288, compound

HRID 1729819
Notes
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Reaction equation

HRID 1729819 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[Cl:20][C:21]1[CH:36]=[CH:35][C:24]2[N:25]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[Cl:20][C:21]1[CH:36]=[CH:35][C:24]2[N:25]([CH:29]3[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][CH:5]([C:13]4[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=4)[C:6]4[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=4)[CH2:33][CH2:34]3)[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 183190411,1'-(4-Chlorobutane-1,1-diyl)bis(4-chlorobenzene)

Product 1

HCID 21500288HCID 21500288, compound

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

A mixture of 4.7 parts of 4-chloro-1,1'-butylidene bis[4-chlorobenzene], 3 parts of 5-chloro-1-(4-piperidyl)- 2-benzimidazolinone, 3.7 parts of sodium carbonate and 100 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, water is added and the layers are separated. The organic layer is dried, filtered and evaporated. The residue is purified by column-chromatography over silicagel, using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane, yielding 5-chloro-1-{1-[4,4-bis(4-chlorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 165.4° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silicagel
  7. additiona mixture of trichloromethane and 5% of methanol as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-d3218032e3ac44eba7bc94b81b49ac45
Source dataset
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03989707

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes