Hydrochloric Acid → 1-(2-Hydroxyethyl)-5-methyl-1H-benzo[d]imidazol-2(3H)-one

HRID 258833Notes

Reaction equation

HRID 258833 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=2[N:6](C(C)=C)[C:5]1=[O:17].Cl>C(O)C>[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=2[NH:6][C:5]1=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214248201,3-dihydro-1-(2-hydroxyethyl)-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 214248171-(2-Hydroxyethyl)-5-methyl-1H-benzo[d]imidazol-2(3H)-oneYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 46 parts of 1,3-dihydro-1-(2-hydroxyethyl)-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-one in 168 parts of ethanol are added 48 parts of hydrochloric acid solution and the whole is stirred for 2 hours at room temperature. The reaction mixture is evaporated and the residue is stirred in 250 parts of water. The precipitated product is filtered off, washed with 2,2'-oxybispropane and dried, yielding 22.3 parts (58%) of 1,3-dihydro-1-(2-hydroxyethyl)-5-methyl-2H-benzimidazol-2-one; mp. 158.7° C.

Workup

  1. customThe reaction mixture is evaporated
  2. stirringthe residue is stirred in 250 parts of water
  3. filtrationThe precipitated product is filtered off
  4. washwashed with 2,2'-oxybispropane
  5. customdried

Sources & evidence

ORD record
ord-11e47cbd648a493a970925d00abd5d66
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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