Sodium hydride → 1-(4,5-Dihydro-2-thiazolyl)-1,3-dihydro-3-(2-thienylmethylene)-2H-indol-2-one

HRID 1414866Notes

Reaction equation

[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18].Cl[CH2:20][CH2:21][N:22]=[C:23]=[S:24]>O1CCCC1>[S:24]1[CH2:20][CH2:21][N:22]=[C:23]1[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[CH:8][C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[C:10]1=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of NaH (0.51 gm; 21.1 mmole) in dry tetrahydrofuran (100 ml) is added dropwise a solution of 3-(2-thienylmethylene)-indolin-2-one prepared as described above (4.0 gm; 17.6 mmole) in dry tetrahydrofuran (100 ml). The resultant solution is stirred at room temperature for another hour, after which, it is cooled to 0° C in an ice bath, and a solution of chloroethylisothiocyanate (2.2 gm; 17.6 mmole) in dry tetrahydrofuran (50 ml) is added. The mixture is then heated at reflux temperature for 3.5 hours.

Workup

customprepared
temperatureThe mixture is then heated
temperatureat reflux temperature for 3.5 hours

Sources & evidence

ORD record: ord-6c537529e821401cb493e0ebe8fccf11
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04002749

Reaction notes

Loading…