Acetic Acid → HCID 86617512, compound

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].N=C(N[C:32](=[O:38])[O:33][CH2:34][CH2:35][CH2:36][Cl:37])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:33][CH2:34][CH2:35][CH2:36][Cl:37])=[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

Reactant 4

HCID 176Acetic Acid

HCID 14798Sodium Hydroxide

HCID 67044654HCID 67044654, compound

HCID 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+).