Hydrochloric Acid → HCID 69659015, compound

HRID 1829043Notes

Reaction equation

HRID 1829043 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[Cl:26][CH2:27][CH2:28][N:29]([CH3:40])[C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[C:35](=O)[O:34][CH2:33]2.Cl>C(COC)OC>[Cl:26][CH2:27][CH2:28][N:29]([CH3:40])[C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[C:35](=[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]1=[O:10])[O:34][CH2:33]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 220614475-[(2-Chloroethyl)(methyl)amino]-2-benzofuran-1(3H)-oneHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 69659015HCID 69659015, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of oxindole (0.739 g, 5.55 mmol) in anhydrous dimethoxyethane (10 ml) under nitrogen was added 1.0M LiHMDS/THF solution (14.0 ml, 14.0 mmol). The mixture was stirred at room temperature for 10 minutes, and 5-[(2-chloro-ethyl)-methyl-amino]-3H-isobenzofuran-1-one (1.0 g, 4.4 mmol) was added. The mixture was stirred at room temperature for 3 hours and was then poured into 1M HCl aqueous solution (300 ml) with stirring. The resulting mixture was heated at 40° C. for 30 minutes. The solid was filtered, washed with water and dried under vacuum to afford 3-{5-[(2-chloro-ethyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-1,3-dihydro-indol-2-one as a yellow solid (1.20 g, 79%).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. stirringwith stirring
  3. temperatureThe resulting mixture was heated at 40° C. for 30 minutes
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-fede22b9bc1f4e92872e50888515507a
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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