Sodium hydride → HCID 15678607, compound

HRID 1534780Notes

Reaction equation

HRID 1534780 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH3:20])[C:12](=[O:21])[NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:11]2[N:10]=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH3:20])[C:12]2=[O:21])=[O:28])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 678794-Fluorobenzoyl chlorideHCID 15678606HCID 15678606, compound

Product 1

HCID 15678607HCID 15678607, compound

Procedure

To a suspension of NaH (70 mg of NaH was washed with hexane several times dispersed in 50% mineral oil) in 4ml of DNF is added a solution of 1,3-dihydro-5-phenyl-1-methyl-2H-1,3,4-benzotriazepine-2-one (251 mg) in 5 ml DMP under nitrogen atmosphere. After gas evolution ceased, 0.13 ml 4-fluorobenzoyl chloride is added and the mixture is stirred at room temperature overnight (about 12-6 hours). Solvent is removed in vacuo to a dryness and the residue is partitioned between ethylacetate and water. Organic layer is washed with aq.NaHCO3, water, then dried over MgSO4. After evaporation of solvent, the residue is recrystallized using methanol as a solvent. About 97mg of a product is obtained. TLC: (Silica gel - Chloroform/acetone=9:1, Rf.=0.52).

Workup

  1. customSolvent is removed in vacuo to a dryness
  2. customthe residue is partitioned between ethylacetate and water
  3. washOrganic layer is washed with aq
  4. dry with materialNaHCO3, water, then dried over MgSO4
  5. customAfter evaporation of solvent
  6. customthe residue is recrystallized

Sources & evidence

ORD record
ord-f1019bd19f2d4bfb9b5d9a37474d38ad
Source dataset
uspto-grants-1992_02
Patent number
US05091381

Reaction notes

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