Reaction #4538

ord-e962f65fda1a436697d07c873020f372

Reaction equation

O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O
3-formyl-5-dichloromethyl-2-phthalimidopyrazine
Cl.NO
hydroxylamine hydrochloride
O
water
→
O=C1c2ccccc2C(=O)N1C1N=CC(C(Cl)Cl)=NC1=NO
colorless crystals
Yield 67.4%
O=C1c2ccccc2C(=O)N1C1N=CC(C(Cl)Cl)=NC1=NO
3-oximino-5-dichloromethyl-2-phthalimidopyrazine
Yield 67.4%

Reactants

O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O
3-formyl-5-dichloromethyl-2-phthalimidopyrazine
Cl.NO
hydroxylamine hydrochloride
O
water

Reagents

None

Solvents

CS(C)=O
dimethyl sulfoxide

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationthe mixture was filtered
  2. 2
    Washthe filtrate was washed with a little diethyl ether

Procedure

A solution of 10 g of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine in 50 ml of dimethyl sulfoxide was heated at 50° C., 7 g of hydroxylamine hydrochloride were added, and the mixture was stirred for 15 minutes at 70° C. Thereafter, 700 ml of water were added to the reaction solution, the mixture was filtered and the filtrate was washed with a little diethyl ether. 6.8 g of colorless crystals (65%) of 3-oximinodichloromethyl-2-phthalimidopyrazine were obtained. 1H-NMR (270 MHz, DMSO-d6): δ7.7 (s, 1H), 8.0 (m, 4H), 8.3 (s, 1HO), 9.1 (s, 1H), 12.0 (s, OH).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04725689uspto-grants-1988_02