Water → HCID 23500388, compound

HRID 1862519Notes

Reaction equation

HRID 1862519 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-ed9e9de17a254fb6b63a3e0f9928d01c
Source dataset
uspto-grants-2003_03
Patent number
US06538022B1

Reaction notes

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