Sodium hydride → Carbamothioic acid, dimethyl-, O-[2-(2-cyanobenzoyl)phenyl] ester

HRID 1087718Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11])=[O:7].[CH3:20][N:21]([CH3:25])[C:22](Cl)=[S:23]>O1CCCC1>[CH3:20][N:21]([CH3:25])[C:22](=[S:23])[O:3][C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[C:6](=[O:7])[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

Conditions

Temperature: 50 °C

Procedure

1 g (0.041 mol) of sodium hydride is added in small amounts to a solution of 6.7 g (0.030 mol) of the 2-(2-hydroxybenzoyl)benzonitrile obtained in Preparation VIIIc in 200 ml of tetrahydrofuran. The mixture obtained is stirred for 1 hour at 50° C. The reaction medium is cooled to room temperature and a solution of 4.6 g (0.037 mol) of dimethylthiocarbamoyl chloride in 50 ml of tetrahydrofuran is added. The mixture obtained is stirred for 3 hours at room temperature and then hydrolyzed with an ice/water mixture. Extraction is carried out with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and then evaporated under reduced pressure. 6 g of the expected product (yield: 64.5%) are obtained after crystallization from ether.

Workup

customThe mixture obtained
temperatureThe reaction medium is cooled to room temperature
customThe mixture obtained
stirringis stirred for 3 hours at room temperature
extractionExtraction
customThe organic phase obtained
washis washed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-c7ffb3d4b2d848aaacee96c734d588e4
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960758

Reaction notes

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