Thiophenol → HCID 470704, compound

HRID 724985Notes

Reaction equation

HRID 724985 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH3:31])[C:16](=[O:30])[C:17]3[CH:27]=[C:26]([CH2:28]Cl)[CH:25]=[N:24][C:18]=3[N:19]([CH2:22][CH3:23])[C:20]=2[N:21]=1>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH3:31])[C:16](=[O:30])[C:17]3[CH:27]=[C:26]([CH2:28][S:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:25]=[N:24][C:18]=3[N:19]([CH2:22][CH3:23])[C:20]=2[N:21]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 470704HCID 470704, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of thiophenol (0.16 mL, 1.6 mmol) in N,N-dimethylformamide (15 mL) was treated with sodium hydride (60% wt, 62 mg, 1.6 mmol). After stirring 15 minutes the 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.50 g, 1.5 mmol) was added and the mixture was stirred for 18 hours more. The excess thiolate was quenched with methanol and the mixture was diluted with aqueous sodium bicarbonate and extracted with dichloromethane. The organics were dried over sodium sulfate, filtered, concentrated and the residue was purified by flash chromatography (hexanes/ethyl acetate) and recrystallization from hexanes/ethyl acetate to give the title compound (0.378 g, 62%), m.p. 92°-93° C.

Workup

  1. additionwas added
  2. customThe excess thiolate was quenched with methanol
  3. additionthe mixture was diluted with aqueous sodium bicarbonate
  4. extractionextracted with dichloromethane
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by flash chromatography (hexanes/ethyl acetate) and recrystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-42bf2efd292548c9bff167807ad2c456
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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