Hydrazine hydrate (1:1) → HCID 117697935, compound

HRID 1778523Notes

Reaction equation

HRID 1778523 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH:18]2[CH2:19][C:20](=O)[CH2:21][CH:14]1[CH2:15][O:16][CH2:17]2)(=[O:12])=[O:11])([O-:3])=[O:2].C(OC([N:32]([CH3:34])C)N(C)C)(C)(C)C.[NH2:35]N.O>O1CCOCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH:18]2[CH2:17][O:16][CH2:15][CH:14]1[C:21]1[CH:34]=[N:32][NH:35][C:20]=1[CH2:19]2)(=[O:11])=[O:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 117697629HCID 117697629, compound

Product 1

HCID 117697935HCID 117697935, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of compound 107b (4.9 g, 15 mmol, 1.0 eq) and tert-butoxy-N,N,N′,N′-tetra-methyl-methanediamine (3.92 g, 22.5 mmol, 1.5 eq) in dioxane (50 mL) was stirred at 60° C. for 16 h, then the solvent was removed in vacuo, the residue was dissolved in EtOH (50 mL), NH2NH2.H2O (3.5 mg, 75 mmol, 5.0 eq) was added and then stirred at 60° C. for 2 h. The reaction mixture was concentrated and then purified by silica gel (EA/PE=1:2) to give 12-(2-Nitro-benzenesulfonyl)-10-oxa-4,5,12-triaza-tricyclo[6.3.1.0*2,6*]dodeca-2(6),3-diene 107c as a slight yellow oil, 1.57 g, yield: 29.8%. MS: calc'd (MH+) 351, measured (MH+) 351.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOH (50 mL)
  3. stirringstirred at 60° C. for 2 h
  4. concentrationThe reaction mixture was concentrated
  5. custompurified by silica gel (EA/PE=1:2)

Sources & evidence

ORD record
ord-8f4a53925b0441a98f3a4929d21b59f5
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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