Ammonia → HCID 12317899, compound

HRID 1729602Notes

Reaction equation

HRID 1729602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-])=[O:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH2:22][O:23][CH3:24])[C:11](=[O:25])[CH2:10][N:9]=1.O1CCCC1.O.O.O.C([O-])(=O)C.[Na+].N>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([NH:19][OH:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH2:22][O:23][CH3:24])[C:11](=[O:25])[CH2:10][N:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 12317896HCID 12317896, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12317899HCID 12317899, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.6 g. (0.01 mol) of 5-(2-chlorophenyl)-1,3-dihydro-1-methoxymethyl-7-nitro-2H-1,4-benzodiazepin-2-one, 100 ml. of tetrahydrofuran, 50 ml. of methanol, 13.6 g. of sodium acetate trihydrate and 11.25 g. of stannous chloride dihydrate was stirred under nitrogen for 5 hours. 500 ml. of methylene chloride and 10 ml. of concentrated ammonia was added. The inorganic material was separated by filtration. The filtrate was washed with 1N sodium hydroxide solution, dried over sodium sulfate and evaporated. Crystallization of the residue from methylene chloride/ether gave light yellow product with m.p. 205°-208° dec. For analysis it was recrystallized from 2 -propanol/tetrahydrofuran.

Workup

  1. additionA mixture of 3.6 g
  2. customThe inorganic material was separated by filtration
  3. washThe filtrate was washed with 1N sodium hydroxide solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customCrystallization of the residue from methylene chloride/ether
  7. customgave light yellow product with m.p. 205°-208° dec
  8. customFor analysis it was recrystallized from 2 -propanol/tetrahydrofuran

Sources & evidence

ORD record
ord-1754616109ad482189d48b0d741d3f80
Source dataset
uspto-grants-1976_11
Patent number
US03989681

Reaction notes

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