Water → HCID 54219580, compound

HRID 1382921Notes

Reaction equation

HRID 1382921 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH2:11][CH2:12][CH2:13][N:14]([CH3:25])[C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:9]=1[CH2:11][CH2:12][CH2:13][N:14]([CH3:25])[C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 54569307HCID 54569307, compound

Product 1

HCID 54219580HCID 54219580, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.1 g (59 mmol) of benzyl [3-[(2-aminophenyl)carbamoyl]propyl]methylcarbamate are dissolved in 450 ml of toluene and treated with 7 g (37 mmol) of p-toluenesulphonic acid. The reaction mixture is thereafter heated to reflux for 2 hours, whereby the water formed is removed from the reaction mixture by means of a water separator. After evaporation and dissolution of the residue in ethyl acetate the solution is washed twice with saturated aqueous sodium bicarbonate solution and twice with saturated aqueous soiium chloride solution. The organic phase is dried over magnesium sulphate and evaporated. Chromatography of the crude product on silica gel with ethyl acetate as the elution agent yields 11 g (58%) of benzyl [3-(2-benzimidazolyl)propyl]methylcarbamate, m.p. 83°-86°.

Workup

  1. temperatureThe reaction mixture is thereafter heated
  2. temperatureto reflux for 2 hours
  3. customis removed from the reaction mixture by means of a water separator
  4. customAfter evaporation and dissolution of the residue in ethyl acetate the solution
  5. washis washed twice with saturated aqueous sodium bicarbonate solution and twice with saturated aqueous soiium chloride solution
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-cd818dbe5dc943b2b0cacec9c061fb52
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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