Water → HCID 23500388, compound

HRID 1835688Notes

Reaction equation

HRID 1835688 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][CH:5]([C:11]([CH3:13])=O)[C:6]([O:8]CC)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[NH2:23].CS(O)(=O)=O.O>C1(C)C(C)=CC=CC=1>[CH3:28][O:27][C:25]1[CH:26]=[C:20]([O:19][CH3:18])[CH:21]=[C:22]2[C:24]=1[C:11]([CH3:13])=[C:5]([CH2:4][C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[F:1])[C:6](=[O:8])[NH:23]2

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 663013,5-DimethoxyanilineHCID 2758957Ethyl 2-[(2-fluorophenyl)methyl]-3-oxobutanoate

Product 1

HCID 23500388HCID 23500388, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
160 °C

Procedure

Ethyl 2-(2-fluorobenzyl)acetoacetate (2.5 g) in xylene (1 ml) was heated to 150° C. and 3,5-dimethoxyaniline (1.46 g) in xylene (4 ml) was added in small portions during 30 minutes. The reaction mixture was heated at 160° C. for 3 hours and then cooled to room temperature. Methanesulfonic acid (1.7 ml) was added and the mixture was stirred at ambient temperature for 30 minutes. Water was added and the precipitate filtered and dried. The product was triturated with warm ethanol. Yield 0.64 g (21%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe precipitate filtered
  3. customdried
  4. customThe product was triturated with warm ethanol

Sources & evidence

ORD record
ord-86bfa7e4d1f9432f9109239beedc87c6
Source dataset
uspto-grants-2004_08
Patent number
US06774103B1

Reaction notes

Loading…