Trifluoroacetic acid → HCID 53939074, compound

HRID 1493629Notes

Reaction equation

HRID 1493629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[NH2:9])=[CH:4][C:3]=1[CH3:15].[O-:16][C:17]#[N:18].[Na+].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[NH2:18][C:17]([NH:9][N:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:15])[CH:4]=1)=[O:16]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 54312551HCID 54312551, compound2×

Product 1

HCID 53939074HCID 53939074, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl [1-(4-fluoro-3-methylphenyl)hydrazino]acetate (Intermediate 64, 0.8, 38 mml), sodium cyanate (0.84 g, 0.0129 mol) and trifluoroacetic acid (0.95 ml, 0.0114 mol) in toluene (15 ml) was stirred under nitrogen at room temperature for 24 hours. The mixture was poured into 8% sodium bicarbonate solution (40 ml) and extracted with ethyl acetate (2×30 ml). The organic extract was dried (MgSO4) and evaporated to give a red oil. This was crystallised by trituration with ether to give a white solid (Intermediate 65, 228 mg; 24%), m.p. 132°-133° C.

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customto give a red oil
  6. customThis was crystallised by trituration with ether

Sources & evidence

ORD record
ord-d6da85e5064247109fbfa82355b6cc2e
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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