Trifluoroacetic acid → HCID 19829888, compound

HRID 1493618Notes

Reaction equation

HRID 1493618 reaction equation
FC(F)(F)C(O)=O.[O-:8][C:9]#[N:10].[Na+].NN.[CH2:14]([O:18][C:19]1[CH:20]=[C:21]([N:25]([CH2:27][C:28]([O:30]C)=O)[NH2:26])[CH:22]=[CH:23][CH:24]=1)[CH2:15][CH2:16][CH3:17]>C1(C)C=CC=CC=1>[CH2:14]([O:18][C:19]1[CH:20]=[C:21]([N:25]2[CH2:27][C:28](=[O:30])[NH:10][C:9](=[O:8])[NH:26]2)[CH:22]=[CH:23][CH:24]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 517096Sodium CyanateHCID 54448601HCID 54448601, compound

Product 1

HCID 19829888HCID 19829888, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (1.2 ml, 15.5 mmol) was added to a suspension of sodium cyanate (1.17 g, 18.0 mmol) and hydrazine (Intermediate 47 1.30 g, 5.15 mmol) in toluene (17 ml) at room temperature and stirred for 2 h. The reaction was quenched with sodium bicarbonate solution, extracted with ethyl acetate and washed with sodium bicarbonate, water and brine, dried (Na2SO4) and concentrated to afford the urea intermediate as a brown oil. A portion of this crude urea (0.65 g, 2.2 mmol) was taken up in methanol (10 ml) and treated with sodium methoxide (0.48 g, 8.8 mmol) at room temperature for 2 h. The reaction was quenched (pH 6.5 buffer), extracted with ethyl acetate, washed with water followed by brine, dried (Na2SO4) and concentrated to afford a red oil which was triturated with ether to afford a pale brown solid (105 mg, 18%), m.p. 100°-105°.

Workup

  1. customThe reaction was quenched with sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a25a102301cb4b2289eaec9b31fdcb7e
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

Loading…