Ethyl 3-(2-amino-3,5-bis(trifluoromethyl)phenylamino)-3-oxopropanoate → ethyl 2-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)acetate

HRID 641592Notes

Reaction equation

HRID 641592 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:3]=1[NH:16][C:17](=O)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)(=O)C.C1COCC1>[F:15][C:12]([F:13])([F:14])[C:5]1[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]2[NH:1][C:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:16][C:3]=2[CH:4]=1

Participants

3

Reactant 1

HCID 86595108Ethyl 3-(2-amino-3,5-bis(trifluoromethyl)phenylamino)-3-oxopropanoate

Product 1

HCID 178470769ethyl 2-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)acetateYield 81.8%

Reagents, catalysts & solvents 1

HCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(2-amino-3,5-bis(trifluoromethyl)phenylamino)-3-oxopropanoate (330 mg, 0.92 mmol) in 3:1 acetic acid/THF (4 mL) was heated at reflux for 18 h. The mixture was concentrated in-vacuo, and the residue was purified over silica gel, eluting with 20%-30%-40% EtOAc/heptane, to yield 256 mg of a colorless oil as product. 1H NMR (500 MHz, DMSO) δ ppm 1.20 (m, 3 H) 4.11 (m, 4 H) 7.82 (m, 1 H) 8.28 (m, 1 H) 13.37 (m, 1 H).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationThe mixture was concentrated in-vacuo
  3. customthe residue was purified over silica gel
  4. washeluting with 20%-30%-40% EtOAc/heptane

Sources & evidence

ORD record
ord-93943b227908433c880ee52f9521b35e
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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