Hydrazinecarboxylic acid, ethyl ester → ethyl 2-(2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3-yl)hydrazine-1-carboxylate

HRID 633454Notes

Reaction equation

HRID 633454 reaction equation
[CH3:1][C:2]1([CH3:16])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[NH:4][C:3]1=S.[NH:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH2:18]>C(O)C>[CH3:1][C:2]1([CH3:16])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[N:4]=[C:3]1[NH:18][NH:17][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 594105272,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazine-3(4H)-thione

Product 1

HCID 86704541ethyl 2-(2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3-yl)hydrazine-1-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,2-Dimethyl-6-nitro-2H-benzo[b][1,4]oxazine-3(4H)-thione (3 g) and ethyl hydrazinecarboxylate (3.94 g, 3.0 eq.) were suspended in ethanol (50 ml). The reaction mixture was refluxed for 6 hours. The yellow precipitation was filtered and washed with ether to give ethyl 2-(2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3-yl)hydrazine-1-carboxylate (3.37 g, 87% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. customThe yellow precipitation
  3. filtrationwas filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-a243c6e39a7940b0b5715ab7ca54f564
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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