Hydrochloric Acid → HCID 18509770, compound

HRID 1370130Notes

Reaction equation

HRID 1370130 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]2[N:7]([CH:22]3[CH2:27][O:26]C(C)(C)[O:24][CH2:23]3)[C:8](=[O:21])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=3)[C:5]=2[CH:4]=1)#[N:2].Cl>O1CCCC1>[C:1]([C:3]1[CH:31]=[CH:30][C:6]2[N:7]([CH:22]([CH2:23][OH:24])[CH2:27][OH:26])[C:8](=[O:21])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=3)[C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18509868HCID 18509868, compound

Product 1

HCID 18509770HCID 18509770, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-cyano-3-(3,4-dimethoxybenzyl)-1-(2,2-dimethyl-1,3-dioxan-5-yl)-2,3-dihydro-1H-benzimidazol-2-one (140 mg) in tetrahydrofuran (2 mL) was added 1 N-hydrochloric acid (1.5 mL), and the mixture was stirred at ambient temperature for 8 hours. After evaporation of the solvent, the residue was partitioned between water and a mixture of chloroform and methanol (10:1). The separated organic layer was washed with brine and dried over magnesium sulfate. After evaporation of solvent, the residue was subjected to a preparative thin-layer chromatography eluting with a mixture of chloroform and methanol (10:1). The obtained substance was triturated with diethyl ether to give 5-cyano-3-(3,4-dimethoxybenzyl)-1-[2-hydroxy-1-(hydroxymethyl)ethyl]-2,3-dihydro-1H-benzimidazol-2-one (92 mg) as powders.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between water
  3. additiona mixture of chloroform and methanol (10:1)
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of solvent
  7. washeluting with a mixture of chloroform and methanol (10:1)
  8. customThe obtained substance was triturated with diethyl ether

Sources & evidence

ORD record
ord-7602fae09bf34db4806f4aaf365a481e
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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