Potassium Hydroxide → HCID 15718522, compound

HRID 1087714Notes

Reaction equation

[OH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=[O:5].[OH-].[K+].[CH3:20][N:21]([CH3:25])[C:22](Cl)=[S:23]>O.CC(C)=O>[CH3:20][N:21]([CH3:25])[C:22](=[S:23])[O:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4](=[O:5])[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

15 g (0.0672 mol) of the 4-(2-hydroxybenzoyl)benzonitrile obtained in Preparation IVb are suspended in a mixture of 150 cm3 of water and 100 cm3 of acetone, 4.15 g (0.0735 mol) of potassium hydroxide are then added and the resulting reaction mixture is stirred and heated for 20 minutes at 50° C. (a red coloration appears, followed by complete dissolution). The solution obtained is cooled to 0° C., a solution of 9.14 g (0.074 mol) of dimethylthiocarbamoyl chloride in 80 ml of acetone is added and the resulting mixture is stirred at room temperature for 3 hours. The reaction medium is hydrolyzed. The precipitate formed is filtered off and then triturated in ether. 17.4 g of the expected product are obtained in the form of a beige solid (yield: 84%).

Workup

additionare then added
customthe resulting reaction mixture
dissolutionfollowed by complete dissolution)
customThe solution obtained
temperatureis cooled to 0° C.
stirringthe resulting mixture is stirred at room temperature for 3 hours
customThe precipitate formed
filtrationis filtered off
customtriturated in ether

Sources & evidence

ORD record: ord-7ac411af68284b8486cb7f40fe0223a9
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960758

Reaction notes

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