Thionyl Chloride → HCID 15451772, compound

HRID 619701Notes

Reaction equation

HRID 619701 reaction equation
[CH:1]1([CH:4]([NH2:6])[CH3:5])[CH2:3][CH2:2]1.[N+:7]([C:10]1[CH:11]=[C:12]2[C:19](=O)[O:18][C:16](=[O:17])[C:13]2=[N:14][CH:15]=1)([O-:9])=[O:8].S(Cl)(Cl)=O>ClCCCl.C(Cl)Cl>[CH:1]1([CH:4]([N:6]2[C:19](=[O:18])[C:12]3[C:13](=[N:14][CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=3)[C:16]2=[O:17])[CH3:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 5192391-CyclopropylethanamineHCID 15451771HCID 15451771, compound

Product 1

HCID 15451772HCID 15451772, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

11.2 g (0.132 mol) of 1-cyclopropylethylamine were added to a mixture of 22.3 g (0.115 mol) of 5-nitropyridine-2,3-dicarboxylic anhydride in 150 ml of 1,2-dichloroethane at 25a° C with stirring in the course of 8 minutes and the mixture was stirred at 70° C. for 3 hours. After cooling to 25° C., 19.6 g (0.165 mol) of thionyl chloride were added with stirring in the course of 10 minutes and the mixture was stirred at 25° C. for 10 hours and at 70° C for 11/2 hours. The reaction mixture was diluted with 100 ml of methylene chloride and added with stirring to 500 ml of ice-water. The aqueous phase was extracted twice more with methylene chloride. The organic phase was then washed successively with water, saturated sodium hydrogencarbonate and sodium chloride solution and filtered off with suction over neutral alumina. After concentrating, 21.5 g (72% of theory) of the title compound of m.p. 96-99° C. were obtained (active compound Example 1.020).

Workup

  1. stirringthe mixture was stirred at 70° C. for 3 hours
  2. stirringwith stirring in the course of 10 minutes
  3. stirringthe mixture was stirred at 25° C. for 10 hours and at 70° C for 11/2 hours
  4. additionadded
  5. extractionThe aqueous phase was extracted twice more with methylene chloride
  6. washThe organic phase was then washed successively with water, saturated sodium hydrogencarbonate and sodium chloride solution
  7. filtrationfiltered off with suction over neutral alumina
  8. concentrationAfter concentrating

Sources & evidence

ORD record
ord-ce0f21a828654252a313d6ab72964b2d
Source dataset
uspto-grants-1999_09
Patent number
US05959116

Reaction notes

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