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

HRID 1414866
Notes
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Reaction equation

HRID 1414866 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1386612-Chloroethyl IsothiocyanateHCID 3087173-[(Thien-2-yl)methylene]-2-indolinone

Product 1

HCID 536804131-(4,5-Dihydro-2-thiazolyl)-1,3-dihydro-3-(2-thienylmethylene)-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

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

  1. customprepared
  2. temperatureThe mixture is then heated
  3. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes