Tetrahydrofuran → 7-(Hydroxyamino)-1-(methoxymethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1729598Notes

Reaction equation

HRID 1729598 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=[O:16])=[CH:14][C:9]=2[C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:7][CH2:6][C:5]1=[O:24].O1CCCC1.O.O.O.C([O-])(=O)C.[Na+]>CO>[OH:16][NH:15][C:13]1[CH:12]=[CH:11][C:10]2[N:4]([CH2:3][O:2][CH3:1])[C:5](=[O:24])[CH2:6][N:7]=[C:8]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:9]=2[CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65764MotrazepamHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 3248157-(Hydroxyamino)-1-(methoxymethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 33 g. (0.1 mol) of 1,3-dihydro-1-methoxymethyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, 1 l. of tetrahydrofuran, 1 l. of methanol. 113 g. (0.5 mol) of stannous chloride dihydrate and 136 g. (1 mol) of sodium acetate trihydrate was stirred at room temperature for 6 hrs. under an atmosphere of nitrogen. The inorganic salts were separated by filtration over celite. The filtrate was evaporated and the residue was partitioned between methylene chloride and 1N sodium hydroxide solution. The methylene chloride layer was washed with water, dried and evaporated. Crystallization of the residue from methylene chloride/ether yielded light yellow product with m.p. 168°-170°. For analysis it was recrystallized from the same solvents, m.p. 168°-171°.

Workup

  1. additionA mixture of 33 g
  2. customThe inorganic salts were separated by filtration over celite
  3. customThe filtrate was evaporated
  4. customthe residue was partitioned between methylene chloride and 1N sodium hydroxide solution
  5. washThe methylene chloride layer was washed with water
  6. customdried
  7. customevaporated
  8. customCrystallization of the residue from methylene chloride/ether
  9. customyielded light yellow product with m.p. 168°-170°
  10. customFor analysis it was recrystallized from the same solvents, m.p. 168°-171°

Sources & evidence

ORD record
ord-c30b69c9db404cf78dd3876d2ea42ca2
Source dataset
uspto-grants-1976_11
Patent number
US03989681

Reaction notes

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