Trifluoroacetic acid → HCID 53833003, compound

HRID 1493635Notes

Reaction equation

HRID 1493635 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[NH2:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:21][C:22]#[N:23].[Na+].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[NH2:23][C:22]([NH:15][N:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)=[O:21]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 54133208HCID 54133208, compound2×

Product 1

HCID 53833003HCID 53833003, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl [1-[4-phenoxyphenyl]hydrazino]acetate (Intermediate 76, 11 g, 0.004 mol), sodium cyanate (0.9 g, 0136 mol) and trifluoracetic acid (1 ml, 0.0124 mol) in dry toluene (15 ml) was stirred under nitrogen at room temperature for 1 hour. The mixture was poured into 8% sodium bicarbonate solution (75 ml) and extracted with ethyl acetate (2×75 ml). The organic extract was dried (MgSO4) and evaporated to give a pale yellow semi-solid. This was triturated with ether to give the title compound (Intermediate 77) as a white solid (0.6 g, 48%) m.p. 110°-113° C.

Workup

  1. extractionextracted with ethyl acetate (2×75 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customto give a pale yellow semi-solid
  6. customThis was triturated with ether

Sources & evidence

ORD record
ord-d39b6502b54e4b7b8cf725c728bd0ca4
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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