Chlorosuccinimide → HCID 20351121, compound

HRID 2052567Notes

Reaction equation

HRID 2052567 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[S:15])[CH:9]2[CH3:16])([O:3][CH2:4][CH3:5])=[O:2].[Cl:17]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:17][C:9]1([CH3:16])[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:7]=2)[NH:11][C:10]1=[S:15]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20289278HCID 20289278, compound

Product 1

HCID 20351121HCID 20351121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-carboethoxy-3-methylthiooxindole (1.50 g, 7 mmol) and N-chlorosuccinimide (1.25 g, 9.3 mmol) in methylene chloride (150 ml) was stirred at room temperature for 24 hours. The solvent was removed in vacuo, yielding crude 3-chloro-5-carboethoxy-3-methylthiooxindole and the residue was dissolved in tetrahydrofuran and added to a vigorously stirred slurry of red mercuric oxide (1.53 g, 7 mmol) and boron trifluoride etherate (1.00 g, 7 mmol) in 100 ml of 50 percent aqueous tetrahydrofuran. After stirring at room temperature for 1 hour, the red solution was extracted with chloroform. The organic extracts were dried over anhydrous magnesium sulfate, filtered, evaporated, and the residue was chromatographed on silica gel. Elution with chloroform gave 5-carboethoxyisatin (860 mg, 56%) as a yellow solid, mp 205°-207° (recrystallized from ether), ir (KBr) 3265 (NH), 1765 (ester C=O), 1750 (C=O), and 1700 cm-1 (amide C= O); nmr (DMSO-d6) τ-1.00 (1H, b s, NH), 1.80 (d of d, 1H, J4,6 =2 Hz, J6,7 =9 Hz, H6), 1.90 (d, 1H, J4,6 =2H3, H4), 3.20 (d, 1H, J6,7 =9 Hz, H7), 5.65 (q, 2H, CO2CH2CH3), and 8.60 (t, 3H, CO2CH2CH3); mass spectrum m/e obs. 219.0534 (calc. 219.0531).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7484e3901dcf4846b0341bd1f6cda37c
Source dataset
uspto-grants-1980_01
Patent number
US04186132

Reaction notes

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