Trifluoroacetic acid → HCID 53963885, compound

HRID 1493644Notes

Reaction equation

HRID 1493644 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[NH2:10])=[CH:5][C:4]=1[CH3:16].[O-:17][C:18]#[N:19].[Na+].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[NH2:19][C:18]([NH:10][N:9]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:16])[CH:5]=1)=[O:17]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 54059198HCID 54059198, compound2×

Product 1

HCID 53963885HCID 53963885, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl [1-[4-methoxy-3-methylphenyl]hydrazino]acetate (Intermediate 97, 380 mg, 0.0017 mol), sodium cyanate (380 mg, 0.0058 mol) and trifluoroacetic acid (0.4 ml, 0.0052 mol) in dry toluene (10 ml) was stirred under nitrogen and at room temperature for 31/2 hours. It was poured into 8% sodium bicarbonate solution (20 ml) and extracted with ethyl acetate (2×20 ml). The organic extract was dried (MgSO4) and evaporated to give a yellow solid which was triturated with ether and filtered to give the title compound as a yellow solid (237 mg, 52%) m.p. 174°-176° C.

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customto give a yellow solid which
  6. customwas triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5edb58c5119f48929acdc3d055fbfe34
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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