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Oxalyl chloride → HCID 68984731, compound

HRID 2249657
Notes
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Reaction equation

HRID 2249657 reaction equation
[CH2:1]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15](O)=[O:16])=[CH:14][C:9]=2[N:8]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]1=[O:23])[CH2:2][CH:3]([CH3:5])[CH3:4].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:34]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][C:47]([O:49][CH2:50][CH2:51][CH:52]([CH3:54])[CH3:53])=[O:48])[CH2:35][CH:36]([CH3:38])[CH3:37]>C(Cl)Cl.CN(C)C=O>[CH2:1]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([C:43]3[CH:44]=[CH:45][C:40]([O:39][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[C:41]([CH2:46][C:47]([O:49][CH2:50][CH2:51][CH:52]([CH3:54])[CH3:53])=[O:48])[CH:42]=3)=[O:16])=[CH:14][C:9]=2[N:8]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]1=[O:23])[CH2:2][CH:3]([CH3:5])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 17816485HCID 17816485, compoundHCID 17816487HCID 17816487, compound

Product 1

HCID 68984731HCID 68984731, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.17 g of 1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylic acid in 9 ml of methylene chloride are added 60 μl of oxalyl chloride and 20 μl of N,N-dimethylformamide successively. The mixture thus obtained is stirred at ambient temperature for 2 hours. Then, 0.42 g of aluminum chloride and 0.38 g of isopentyl 2-(2-isopentyloxyphenyl)acetate are successively added at ambient temperature, and the mixture thus obtained is stirred at the same temperature as above for 30 minutes. The reaction mixture is added to a mixture of methylene chloride and ice water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 0.29 g of isopentyl 2-[5-[(1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)carbonyl]-2-(isopentyloxy)phenyl]acetate as a light yellow oily product.

Workup

  1. customThe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred at the same temperature as above for 30 minutes
  4. customthe organic layer is separated
  5. customThe organic layer thus obtained
  6. washis washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customThe residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-bb8cf0bef98145f7961495afb18dba85
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07314888B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes