Ethanol → Ethyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-(ethylthioureido)benzoate

HRID 725137Notes

Reaction equation

HRID 725137 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].[CH2:29]([N:31]=[C:32]=[S:33])[CH3:30].C(O)C>C(OCC)(=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][NH:13][C:3]2[C:2]([NH:1][C:32]([NH:31][CH2:29][CH3:30])=[S:33])=[CH:12][CH:11]=[CH:10][C:4]=2[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:16][CH:17]=1)#[N:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 10966Ethyl isothiocyanateHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate

Product 1

HCID 53943039Ethyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-(ethylthioureido)benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (1.61 g), ethyl isothiocyanate (1.5 ml) and ethanol (1 ml) was stirred at room temperature for 3 days. The reaction mixture was dissolved in ethyl acetate and the solution was washed with water, dried and concentrated to dryness to give crystals. Recrystallization from ethyl acetate-hexane afforded pale yellow crystals (1.92 g, 91%), m.p. 108°-110° C.

Workup

  1. washthe solution was washed with water
  2. customdried
  3. concentrationconcentrated to dryness
  4. customto give crystals
  5. customRecrystallization from ethyl acetate-hexane afforded pale yellow crystals (1.92 g, 91%), m.p. 108°-110° C.

Sources & evidence

ORD record
ord-b04ca5e0470948d9bdcc59efb542f443
Source dataset
uspto-grants-1998_01
Patent number
US05705517

Reaction notes

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