Water → HCID 66847496, compound

HRID 1486258Notes

Reaction equation

HRID 1486258 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([CH3:5])=[O:4].[NH2:8][CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10]O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:5][C:3]1([C:2]([F:7])([F:6])[F:1])[NH:8][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 9871Methyl trifluoromethyl ketoneHCID 924662-Amino-2-phenylethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 66847496HCID 66847496, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

55.13 g (492.0 mmol) of 1,1,1-trifluoroacetone in toluene (1.35 l) were admixed with 45 g (328.0 mmol) of rac-2-amino-2-phenylethanol and 8.24 g (32.8 mmol) of pyridinium p-toluenesulphonate. The reaction mixture was boiled under reflux on a water separator for 16 h. The mixture was cooled to 0° C., and the solids formed were filtered off and dried under high vacuum. This gave 68.6 g (77% of theory, purity 85%) of the target compound.

Workup

  1. customthe solids formed
  2. filtrationwere filtered off
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-d556e638ce164cf3833919bbeba18f12
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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