Sodium hydride → HCID 21485072, compound

HRID 1414719Notes

Reaction equation

HRID 1414719 reaction equation
[H-].[Na+].[N:3]1[NH:4][C:5](=[O:21])[N:6]2[C:12]=1[C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[O:9][C:8]1[CH:17]=[CH:18][CH:19]=[CH:20][C:7]2=1.[H][H].F[C:25]1[CH:26]=[C:27]([Cl:31])[CH:28]=[CH:29][CH:30]=1>O.CN(C)C=O>[Cl:31][C:27]1[CH:26]=[C:25]([N:4]2[C:5](=[O:21])[N:6]3[C:7]4[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=4[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[C:12]3=[N:3]2)[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 2230871-Chloro-3-fluorobenzeneHCID 21485071HCID 21485071, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21485072HCID 21485072, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 1.12 g. (0.025 mole) of a 57% mineral oil dispersion of sodium hydride in 20 ml. of dry dimethylformamide is added a solution of 4.25 g. (0.017 mole) of dibenzo[b,f][1,2,4]triazolo[4,3-d][1,4]-oxazepin-3(2H)-one in 10 ml. of dry dimethylformamide at a rate so as to maintain the temperature of the reaction mixture at Ca. 32°-35° and to maintain a steady evolution of H2. After the addition is complete, the mixture is heated to about 50° until the evolution of hydrogen ceases. 2.76 g. (0.021 mole) of 3-fluoro-chlorobenzene is added to the reaction mixture at a rate so as to maintain a temperature of 50°-60°. After the addition is complete, the reaction mixture is stirred at 60°-70° for 3 hours and then at 35° for an additional 12 hours. The reaction mixture is cooled, diluted with a large excess of water and extracted with methylene chloride. The solvent is evaporated to give the crude title compound which is purified by chromatography as described in Example 1c.

Workup

  1. additionTo a stirred suspension of 1.12 g
  2. temperature32°-35° and to maintain a steady evolution of H2
  3. additionAfter the addition
  4. temperatureto maintain a temperature of 50°-60°
  5. additionAfter the addition
  6. waitat 35° for an additional 12 hours
  7. temperatureThe reaction mixture is cooled
  8. extractionextracted with methylene chloride
  9. customThe solvent is evaporated

Sources & evidence

ORD record
ord-b9ba65bc04da48bb91e36154ce55580f
Source dataset
uspto-grants-1977_01
Patent number
US04002639

Reaction notes

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