Phenyl Isothiocyanate → HCID 15027715, compound

HRID 345960Notes

Reaction equation

[C:1]([CH2:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]([O:11]C)=O)#[N:2].[C:13]1([N:19]=[C:20]=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>O1CCCC1.O>[NH2:2][C:1]1[C:3]2[C:4]3[CH:8]=[CH:7][S:6][C:5]=3[C:9](=[O:11])[N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:20]=2[S:21][C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.81 g of methyl 3-cyanomethylthiophene-2-carboxylate and 1.62 g of phenyl isothiocyanate in 30 ml of tetrahydrofuran was added 480 mg of a 60% sodium hydride with stirring at 0° C. in a stream of nitrogen, and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added 1.14 ml of methyl bromoacetate at room temperature, and the mixture was stirred for 3 hours. To the reaction mixture was added 480 mg of a 60% sodium hydride, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 100 ml of water, and precipitates were collected by a filtration. The precipitates were successively washed with water, benzene and n-hexane, and dried over to obtain 3.06 g of the desired product as white crystals.

Workup

stirringthe mixture was stirred for 1 hour at room temperature
stirringthe mixture was stirred for 3 hours
stirringthe mixture was stirred overnight at room temperature
customprecipitates
filtrationwere collected by a filtration
washThe precipitates were successively washed with water, benzene and n-hexane
customdried over

Sources & evidence

ORD record: ord-93d7189a34d64122a633fb28cbed543b
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05059692

Reaction notes

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