Sodium Iodide → HCID 21701443, compound

HRID 1596352Notes

Reaction equation

C(O[CH:5]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:9]2[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:8]=2[NH:7][C:6]1=[O:24])(=O)C.[I-].[Na+].[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K]>CN(C)C=O>[C:27]1(=[O:37])[N:31]([CH:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:9]3[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:8]=3[NH:7][C:6]2=[O:24])[C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3RS)-3-acetoxy-5-(2-fluorophenyl)-9-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (3.60 g), sodium iodide (15.59 g) and potassium phthalimide (2.89 g) in dimethylformamide (25 ml) was stirred at 100° C. for 1 hour. The reaction mixture was poured into ice-water and the resultant precipitate was collected by filtration. After washing with water several times and dried over phosphorus pentoxide under reduced pressure, the crude powder was subjected to column chromatography on silica gel eluting with a mixture of chloroform and methanol (100:1). The fractions containing the desired product were combined and evaporated in vacuo to give (3RS)-3-phthalimido-5-(2-fluorophenyl)-9-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (0.82 g, 18.9% yield) as a crystalline powder.

Workup

filtrationthe resultant precipitate was collected by filtration
washAfter washing with water several times
dry with materialdried over phosphorus pentoxide under reduced pressure
additionthe crude powder was subjected to column chromatography on silica gel eluting with a mixture of chloroform and methanol (100:1)
additionThe fractions containing the desired product
customevaporated in vacuo

Sources & evidence

ORD record: ord-254d6ca1517e4bbfad4501ebd6d0a6e8
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291452B1

Reaction notes

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