Tetrahydrofuran → tert-Butyl 2-((2,2,2-trifluoroethyl)carbamoyl)hydrazinecarboxylate

HRID 1504736Notes

Reaction equation

HRID 1504736 reaction equation
[NH:1]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:2].[F:10][C:11]([F:17])([F:16])[CH2:12][N:13]=[C:14]=[O:15].C1COCC1>C1C=CC=CC=1>[F:10][C:11]([F:17])([F:16])[CH2:12][NH:13][C:14]([NH:2][NH:1][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70091tert-Butyl carbazateHCID 106782311,1,1-Trifluoro-2-isocyanatoethane

Product 1

HCID 86722559tert-Butyl 2-((2,2,2-trifluoroethyl)carbamoyl)hydrazinecarboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of tert-butyl hydrazinecarboxylate (1.0 g, 8 mmol) in anhydrous benzene (10.0 mL) was added 1,1,1-trifluoro-2-isocyanatoethane (1.06 g, 8 mmol) neat via syringe to give a gelatin like mixture. Anhydrous THF was added to give a clear solution which was stirred for 10 minutes, after which time the reaction mixture was evaporated to afford the title compound as a white solid (1.62 g, 79%): 1H NMR (400 MHz, CDCl3) δ 6.63 (s, 1H), 6.40 (d, J=2.2 Hz, 1H), 5.84 (s, 1H), 3.88 (qd, J=9.0, 6.6 Hz, 2H), 1.48 (s, 9H); 19F NMR (376 MHz, CDCl3) δ −73.20. This material is used without further purification.

Workup

  1. customto give a gelatin like mixture
  2. customto give a clear solution which
  3. customafter which time the reaction mixture was evaporated

Sources & evidence

ORD record
ord-70c3e75d93a54be499f363250a8c821a
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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