Sodium Iodide → HCID 57670993, compound

HRID 1364336Notes

Reaction equation

HRID 1364336 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([CH:27]=1)/[CH:7]=[C:8]1/[C:9](=[O:26])[N:10]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:11][C:12](=[O:15])[NH:13][CH2:14]/1.ClC1C=CC(S(N)(=O)=O)=CC=1.C(=O)([O-])O.[Na+].[I-].[Na+].Br[CH2:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH2:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[C:6](/[CH:7]=[C:8]2\[CH2:14][NH:13][C:12](=[O:15])[CH2:11][N:10]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:9]\2=[O:26])[CH:27]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 668244-ChlorobenzenesulfonamideHCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 66935411HCID 66935411, compound

Product 1

HCID 57670993HCID 57670993, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (6E)-6-(5-chloro-2-hydroxybenzylidene)-4-[(4-chlorophenyl)sulfonyl]-1,4-diazepan-2,5-dione (364 mg), synthesized from the compound S21 and 4-chlorobenzenesulfonamide by the similar procedure as with Reference Example 117, Reference Example 122, Example 1, and Example 193, in N,N-dimethylformamide (7.3 ml) solution, sodium hydrogencarbonate (89 mg), sodium iodide (12 mg), and tert-butyl bromoacetate (0.19 ml) were added and the mixture was stirred at room temperature for 17 hours. The reaction solution was diluted with ethyl acetate, then the obtained solution was successively washed with saturated ammonium chloride aqueous solution and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1), then the obtained purified product was recrystallized from hexane/ethyl acetate to obtain the title compound (247 mg).

Workup

  1. additionwere added
  2. washthe obtained solution was successively washed with saturated ammonium chloride aqueous solution and saturated saline
  3. dry with materialdried over with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  6. customthe obtained purified product
  7. customwas recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-d5415e5993a44dc0bb27cdb33c780434
Source dataset
uspto-grants-2011_02
Patent number
US07888348B2

Reaction notes

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