Acetic Acid → HCID 15654675, compound

HRID 612763Notes

Reaction equation

HRID 612763 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:21][CH:20]=2)=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:33]([O-])([O-])([O-])[O:34][CH2:35][CH2:36][CH3:37]>>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]2[C:7]3[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=[CH:16][C:6]=3[N:5]=[C:33]2[O:34][CH2:35][CH2:36][CH3:37])=[CH:20][CH:21]=1)#[N:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 86586169Propyl orthocarbonate

Product 1

HCID 15654675HCID 15654675, compound

Conditions

Temperature
80 °C

Procedure

Acetic acid (0.2 g) was added to a solution of ethyl 3-amino-2-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate (0.9 g) in propyl orthocarbonate (5 ml). The mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated, and the concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate. The solvent was evaporated to give crystals. Recrystallization from ethyl acetate--benzene afforded colorless crystals (0.72 g, 68%), m.p. 90-92° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in ethyl acetate
  3. washThe solution was washed with an aqueous solution of sodium hydrogen carbonate
  4. customThe solvent was evaporated
  5. customto give crystals
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-891e8477f9354b2ebe5aa4e0f6e68e4a
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

Loading…