Benzyl mercaptan → HCID 70976067, compound

HRID 535624Notes

Reaction equation

HRID 535624 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.[C:13]1([CH2:19][SH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[CH2:19]([S:20][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 27751424-chlorophthalazin-1(2H)-one

Product 1

HCID 70976067HCID 70976067, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one (500 mg, 2.77 mmol), phenylmethanethiol (412 mg, 3.32 mmol) and sodium hydride (144 mg, 3.6 mmol) in DMF (30 mL) was stirred at 125 C for 2 hours. The reaction mixture was quenched with water, and extracted with EtOAc (2×). The combined organic layer was washed with water, and concentrated to give 456 mg (61%) of title compound. MS (APCI+) M/Z 269 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layer was washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cece045154ef460988f8c5d3304fbf0c
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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