Hydrazine hydrate (1:1) → HCID 66704640, compound

HRID 424557Notes

Reaction equation

HRID 424557 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][S:16][C:15]2[CH:19]=[CH:20][C:21]([N+:23]([O-])=O)=[CH:22][C:14]1=2)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].O.NN>C(O)C.C(OCC)(=O)C.[Ni]>[NH2:23][C:21]1[CH:20]=[CH:19][C:15]2[S:16][CH2:17][CH2:18][N:13]([CH2:12][CH2:11][N:3]([CH2:1][CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[C:14]=2[CH:22]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66704717HCID 66704717, compound

Product 1

HCID 66704640HCID 66704640, compoundYield 95.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of tert-butyl ethyl(2-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (925 mg, 2.52 mmol) in ethanol (10 mL) was added Raney-Nickel (˜148 mg, 2.52 mmol) followed by hydrazine hydrate (1.225 mL, 25.2 mmol). The resulting mixture was stirred vigorously at 50° C. for 10 minutes. The mixture was then cooled to room temperature, diluted with ethyl acetate, and then washed sequentially with a 1:1 mixture of water and saturated sodium carbonate (3×) and saturated sodium carbonate. The organic phase was dried, filtered, and concentrated giving a red oil (810 mg, 95%); ESI-MS (m/z, %): 338 (MH+, 100), 282 (53), 238 (36).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. washwashed sequentially with a 1:1 mixture of water and saturated sodium carbonate (3×) and saturated sodium carbonate
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82718a8373e44e3f9278653a14275fc6
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

Loading…