Water → HCID 23047272, compound

HRID 2107043Notes

Reaction equation

HRID 2107043 reaction equation
[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2=[O:19].[CH3:20][Mg]Br.CCOCC.O>C1COCC1>[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2([OH:19])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 15111539HCID 15111539, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 23047272HCID 23047272, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (3,6 mmol) 5-(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1H-indole-2,3 dione (Example 12) were dissolved under argon in 25 ml dry THF in a flame dried flask. 12 ml 3M methyl magnesium bromide in ether (10 eq) were added dropwise at 0°-5° C. The mixture was stirred overnight. 50 ml water were added, and extracted with ethyl acetate. The organic layers were washed with water and dried over magnesium sulfate. Purification by chromatography on silica (eluent:methylene chloride/ethyl acetate: 2/1), yielded 300 mg (28%) of the desired compound.

Workup

  1. customdried flask
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customPurification by chromatography on silica (eluent:methylene chloride/ethyl acetate: 2/1)

Sources & evidence

ORD record
ord-bdf8ad240cfe4b2d8f1f5f22731e597f
Source dataset
uspto-grants-1990_06
Patent number
US04933336

Reaction notes

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