Water → HCID 23299848, compound

HRID 1952776Notes

Reaction equation

HRID 1952776 reaction equation
[C:1]1([S:7]([CH3:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[N:20][N:19]=1.O>O1CCCC1.O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C>[C:1]1([S:7]([CH2:9][CH:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[N:19][NH:20]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9207PhthalazineHCID 14516Methyl phenyl sulfoxideHCID 2724682Lithium diisopropylamide

Product 1

HCID 23299848HCID 23299848, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Procedure

A solution of 1 g of methyl phenyl sulphoxide in 14 ml of tetrahydrofuran is added dropwise at 78° C. within 10 min. to 3.93 ml of 2M solution of lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene in 20 ml of tetrahydrofuran. The reaction mixture is stirred for a further 30 min. A solution of 0.928 g of phthalazine in 14 ml of tetrahydrofuran is added dropwise within 10 min. The mixture is stirred at -78° C. for 1 hr., treated with 100 ml of water and extracted 3 times with 50 ml of chloroform. The organic phases are combined, dried over magnesium sulphate, filtered and the filtrate is concentrated. 1.9 g of crude (RS)-1-benzenesulphinylmethyl-1,2-dihydro-phthalazine are isolated as a yellowish oil, MS(ISP): 271.2 (M+H)+.

Workup

  1. stirringThe mixture is stirred at -78° C. for 1 hr
  2. extractionextracted 3 times with 50 ml of chloroform
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-a3a5ba744839461a9244a374bd220b96
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

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