Acetic Acid → HCID 86617512, compound

HRID 2367115Notes

Reaction equation

HRID 2367115 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:26])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[Cl:27][CH2:28][CH2:29][CH2:30][O:31][C:32](=[O:38])NC(=N)SC.[OH-].[Na+].[C:41](O)(=O)[CH3:42]>>[OH:26][C:9]1([C:4]2[CH:5]=[CH:6][C:7]3[N:8]=[C:41]([CH2:42][C:32]([O:31][CH2:30][CH2:29][CH2:28][Cl:27])=[O:38])[NH:1][C:2]=3[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67044654HCID 67044654, compoundHCID 152766194HCID 152766194, compound

Product 1

HCID 86617512HCID 86617512, compoundYield 71%

Procedure

A solution of (3,4-diaminophenyl)-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one) (0.42 g, 1.21 mmol) and 3-chloropropyl[imino(methylthio)methyl]carbamate (0.27 g, 1.31 mmol) in glacial acetic acid (5.0 mL) was heated to 80° C. for 20 minutes. The reaction mixture was poured into ice water and the pH was adjusted to 9 by the addition of 2M aqueous sodium hydroxide. The precipitated product was extracted with ethyl acetate (100 mL) and the organic layer was washed with brine and dried over anhydrous sodium sulfate, followed by the evaporation of the solvent. The resulting crude product was purified by silica gel flash chromatography (chloroform-acetonitrile 95:5 to 9:1 eluent) to give 3-chloropropyl {6-[1-hydroxy-3-oxo-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-yl]-1H-benzimidazol-2-yl}acetate (0.64 g, 71% yield). MS (EI) for C26H23ClN4O4: 491 (MH+).

Workup

  1. extractionThe precipitated product was extracted with ethyl acetate (100 mL)
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfollowed by the evaporation of the solvent
  5. customThe resulting crude product was purified by silica gel flash chromatography (chloroform-acetonitrile 95:5 to 9:1 eluent)

Sources & evidence

ORD record
ord-cae385145da342f68c6845ec86bc5159
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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