Water → HCID 13287916, compound

HRID 1903722Notes

Reaction equation

HRID 1903722 reaction equation
[H-].[Na+].O.[N:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[NH:9][C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]1=2)=[O:5].[CH3:22]I>CN(C)C=O>[CH3:22][N:9]1[C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:6]([N:4]=[O:5])[C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]1=2

Participants

6

Reactant 4

HCID 962Water2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13287906HCID 13287906, compound

Product 1

HCID 13287916HCID 13287916, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.4 g, 50% oil dispersion) was added in small portions to a water cooled solution of 10,11-dihydro-5-nitrosodibenzo[b,e][1,4]diazepin11(5H)-one (13.5 g) in dimethylformamide (200 ml) such that the temperature did not exceed 20° C. After the addition was complete the mixture was stirred at room temperature for 30 minutes and then treated with methyl iodide (7.0 g) added in one lot. The resulting mixture, after being stirred at room temperature for 2 hours, was poured into an excess of ice and water, and extracted with methylene chloride. The methylene chloride extract was washed with water, dried over magnesium sulfate and the solvent evaporated under reduced pressure. The residue, which contained some dimethylformamide, was repeatedly triturated with water until it turned to a crystalline solid. It was filtered off, washed with water and air-dried to yield the title compound, m.p. 95°-98°.

Workup

  1. customdid not exceed 20° C
  2. additionAfter the addition
  3. additionadded in one lot
  4. stirringThe resulting mixture, after being stirred at room temperature for 2 hours
  5. extractionextracted with methylene chloride
  6. extractionThe methylene chloride extract
  7. washwas washed with water
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent evaporated under reduced pressure
  10. customwas repeatedly triturated with water until it
  11. filtrationIt was filtered off
  12. washwashed with water
  13. customair-dried

Sources & evidence

ORD record
ord-7d251f51621842d79520cac0dd1471bc
Source dataset
uspto-grants-1984_03
Patent number
US04438120

Reaction notes

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