Water → HCID 131717532, compound

HRID 1886410Notes

Reaction equation

HRID 1886410 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.Br.Br.[NH:14]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[N:24]([CH2:25][C:26]3[N:27]=[CH:28][S:29][CH:30]=3)[C:23]3[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=3[N:21]=2)[CH2:15]1.[C:35](=[O:38])([O-:37])[O-].[Na+].[Na+].[I-].[K+].[OH2:43]>CC(C)CC(=O)C>[C:11]([OH:10])(=[O:43])[C:35]([OH:37])=[O:38].[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:14]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]3[N:24]([CH2:25][C:26]4[N:27]=[CH:28][S:29][CH:30]=4)[C:23]4[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=4[N:21]=3)[CH2:15]2)=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 875134-(2-Chloroethyl)phenyl methyl etherHCID 19875944HCID 19875944, compound

Product 1

HCID 131717532HCID 131717532, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.1 parts of 1-(2-chloroethyl)-4-methoxybenzene, 6.9 parts of N-(3-pyrrolidinyl)-1-(4-thiazolylmethyl)-1H-benzimidazol-2-amine dihydrobromide, hemihydrate, 8.0 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred for 22 hours at reflux temperature using a water separator. After cooling, the reaction mixture was poured into water. The organic phase was separated, washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (95:5:0.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in 2-propanone. After cooling, the precipitated product was filtered off and dried, yielding 2.0 parts (21.7%) of N-[1-[2-(4-methoxyphenyl) ethyl]-3-pyrrolidinyl]-1-(4-thiazolylmethyl)-1H-benzimidazol-2-amine ethanedioate(1:2); mp. 191.1° C. (compound 121).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane, methanol and ammonium hydroxide (95:5:0.5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. temperatureAfter cooling
  13. filtrationthe precipitated product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-17547cb140f34282a7cb2b931a385d31
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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