Sodium Iodide → HCID 135829358, compound

HRID 963484Notes

Reaction equation

HRID 963484 reaction equation
C(O[CH:5]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=2[NH:7][C:6]1=[O:22])(=O)C.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K].[I-].[Na+]>CN(C)C=O>[CH:9]1([C:10]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:7][C:6](=[O:22])[CH:5]([N:27]3[C:26](=[O:28])[C:25]4=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]4[C:23]3=[O:33])[N:11]=2)[CH2:8][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24194345Phthalimide potassium saltHCID 135829355HCID 135829355, compound

Product 1

HCID 135829358HCID 135829358, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (3RS)-3-acetoxy-5-cyclohexyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (2.00 g) in N,N-dimethylformamide (15 ml) was added potassium phthalimide (1.85 g) under stirring and heated at 60° C. To the mixture was added sodium iodide (12.64 g) and stirred for 3 hours at 100° C. The hot resultant mixture was poured into ice-water to give a crude product. The precipitated crude product was collected by filtration. Dryness under the reduced pressure at 40° C. gave (3RS)-5-cyclohexyl-2,3-dihydro-3-phthalimido-1H-1,4-benzodiazepin-2-one (1.80 g) as an yellow powder, which was used in a following reaction step without further purification.

Workup

  1. stirringstirred for 3 hours at 100° C
  2. customto give a crude product
  3. customThe precipitated crude product
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c232821b2f9549e981d754a71157e4b3
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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