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

HRID 277461Notes

Reaction equation

HRID 277461 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%), n.p. 108-101° 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%)
  6. custom108-101° C.

Sources & evidence

ORD record
ord-db8ba4840d024c34bea2a2f919e376ff
Source dataset
uspto-grants-2002_03
Patent number
US06355808B2

Reaction notes

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