Hydrochloric Acid → HCID 69011379, compound

HRID 1884117Notes

Reaction equation

HRID 1884117 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=1.[C:21](=O)([O-])[OH:22].[Na+].C[CH:27]([C:31](Cl)=[O:32])[C:28](Cl)=[O:29].Cl>C(OCC)(=O)C>[CH3:21][O:22][C:31](=[O:32])[CH2:27][C:28]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=2)=[CH:8][C:9]=1[C:14]([F:15])([F:16])[F:17])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10931669MethylmalonylchlorideHCID 22137911HCID 22137911, compound

Product 1

HCID 69011379HCID 69011379, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.515 g (1.8 mmol) 4-(3-Fluoro-benzyloxy)-2-trifluoromethyl-phenylamine is dissolved in 20 ml ethyl acetate. 0.38 g (4.51 mmol) sodium hydrogencarbonate is added and the mixture cooled in the ice-bath. 0.27 g (2.0 mmol) methyl malonyl chloride, dissolved in 5 ml ethyl acetate is slowly added over a period of about 15 min. The resulting mixture is stirred at room temperature overnight. 10 ml 2M aqueous hydrochloric acid is added, the organic layer separated and dried over magnesium sulfate. Evaporation of the solvent gives a slightly yellow solid which is recrystallised from methanol. Colorless solid, Yield=58%. MS: m/e=386.1 (M++H).

Workup

  1. additionis slowly added over a period of about 15 min
  2. customthe organic layer separated
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgives a slightly yellow solid which
  6. customis recrystallised from methanol

Sources & evidence

ORD record
ord-5d098689b6a44ba897196f3d29eb138b
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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