Water → HCID 13834639, compound

HRID 1732015Notes

Reaction equation

HRID 1732015 reaction equation
[C:1]([CH:3]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]1=2)#[N:2].[CH3:17]I.[H-].[Na+].O>CN(C)C=O>[C:1]([C:3]1([CH3:17])[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]1=2)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13672817HCID 13672817, compound

Product 1

HCID 13834639HCID 13834639, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-cyano-6H-dibenzo[b,d]thiopyran (4.5 g; 0.02 mol) and CH3I (28.4 g; 0.2 mol) in 100 ml of dimethylformamide, 50% NaH (1.5 g; 0.03 mol) was added in small portions. After 16 hours at room temperature the mixture was poured into water and extracted with diethyl ether. The organic phase was washed with water and dried over Na2SO4. Evaporation of the solvent gave 6-cyano-6-methyl-6H-dibenzo[b,d]thiopyran (3.58 g; 0.015 mol; yield 75%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-972393a8f8b84449a4c54ecd797b9d4e
Source dataset
uspto-grants-1986_11
Patent number
US04624949

Reaction notes

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