Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-mercaptobenzimidazole-7-carboxylate

HRID 725135Notes

Reaction equation

HRID 725135 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:17][CH:16]=2)=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:29](=S)(OCC)[S-:30].[Na+]>C(O)C>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:13]2[C:3]3[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][CH:11]=[CH:12][C:2]=3[N:1]=[C:29]2[SH:30])=[CH:16][CH:17]=1)#[N:28]

Participants

4

Reactant 2

HCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 23690437Sodium ethylxanthate

Product 1

HCID 178468776Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-mercaptobenzimidazole-7-carboxylateYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-amino-2-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate (5.6 g) and sodium O-ethyl dithiocarbonate (7.3 g) in ethanol (50 ml) was heated for 8 hours under reflux. The reaction mixture was concentrated and the residue was dissolved in water. The solution was adjusted to pH 3-4 with hydrochloric acid. Precipitating crystals were collected by filtration, followed by recrystallization from ethanol to afford yellow crystals (5.0 g, 80%), m.p. 225°-227° C.

Workup

  1. temperaturewas heated for 8 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in water
  5. customPrecipitating crystals
  6. filtrationwere collected by filtration
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-e6fe41b61e044ffe90a9f93bdb5e3485
Source dataset
uspto-grants-1998_01
Patent number
US05705517

Reaction notes

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