Sodium Carbonate → HCID 53996252, compound

HRID 2051691Notes

Reaction equation

HRID 2051691 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.Cl.[NH:14]1[CH2:18][CH2:17][CH:16]([CH2:19][N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>CC(O)C>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH:8]([OH:9])[CH2:10][N:14]2[CH2:18][CH2:17][CH:16]([CH2:19][N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 915152-((4-Chlorophenoxy)methyl)oxiraneHCID 20379522HCID 20379522, compound

Product 1

HCID 53996252HCID 53996252, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4 parts of (4-chlorophenoxymethyl)oxirane, 5 parts of 1,3-dihydro-1-(3-pyrrolidinylmethyl)-2H-benzimidazol-2-one monohydrochloride, 6 parts of sodium carbonate and 80 parts of 2-propanol is stirred and refluxed for 5 hours. The reaction mixture is cooled, filtered and the filtrate is evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 2.8 parts (35%) of 1-{1-[3-(4-chlorophenoxy)-2-hydroxypropyl]-3-pyrrolidinylmethyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 129° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-e5744262bbbc47ad9c4465fa16261a6b
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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