Allyl Isothiocyanate → 2-(2,6-dichlorophenylamino)-3-methyl-5-(3-allyl-thioureido)-3H-benzimidazole-4-carboxylic acid amide

HRID 2296719Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:10][C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:8]([CH3:9])[C:4]=2[C:3]=1[C:21]([NH2:23])=[O:22].[CH2:24]([N:27]=[C:28]=[S:29])[CH:25]=[CH2:26]>CN(C=O)C.[Cl-].[Na+].O>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[NH:10][C:7]1[N:8]([CH3:9])[C:4]2[C:3]([C:21]([NH2:23])=[O:22])=[C:2]([NH:1][C:28]([NH:27][CH2:24][CH:25]=[CH2:26])=[S:29])[CH:20]=[CH:19][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 100 mg (0.286 mmol) of 5-amino-2-(2,6-dichlorophenylamino)-3-methyl-3H-benzimidazole-4-carboxylic acid amide (Example 7) and 114 mg (1.15 mmol) of allyl isothiocyanate in DMF was warmed at 45° C. for 48 h. The reaction was diluted with 30 mL of brine and extracted with four 15 mL portions of EtOAc. The combined organic layers were washed with five 15 mL portions of brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel (MeOH-methylene chloride, first 2:98, then 4:96, then 5:95) to afford 66 mg (51%) of 2-(2,6-dichlorophenylamino)-3-methyl-5-(3-allyl-thioureido)-3H-benzimidazole-4-carboxylic acid amide.

Workup

extractionextracted with four 15 mL portions of EtOAc
washThe combined organic layers were washed with five 15 mL portions of brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customchromatographed on silica gel (MeOH-methylene chloride, first 2:98

Sources & evidence

ORD record: ord-d15c76405b0c4556a89ad10f7355477c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489328B2

Reaction notes

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