Water → HCID 23500388, compound

HRID 1386241Notes

Reaction equation

HRID 1386241 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-137f7495e9074fb1b32bce85dd91510b
Source dataset
uspto-grants-2001_07
Patent number
US06265421B1

Reaction notes

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