Dichloromethane → HCID 19046782, compound

HRID 1781634Notes

Reaction equation

HRID 1781634 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)[NH2:5].Cl[O:13][C:14](C)(C)C.C(O[C:21](=[S:24])CC)C.[CH2:25](N(CC)CC)C.Cl[CH2:33][Cl:34]>>[Cl:34][C:33]1[CH:25]=[C:6]2[C:4](=[CH:3][CH:2]=1)[NH:5][C:14](=[O:13])[C:8]([S:24][CH3:21])=[C:7]2[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 5

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 2196153-chloro-5-nitroanilineHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetate

Product 1

HCID 19046782HCID 19046782, compoundYield 40%

Procedure

14.2 g (82.3 mmol) of 3-chloro-5-nitro-aniline am dissolved under nitrogen at -65° in 235 ml of dichloromethane, and a solution of 9.8 ml (82.3 mmol) of tert-butyl hypochlorite in 30 ml of dichloromethane is added dropwise thereto. The mixture is then stirred for 10 minutes at -65° and then a solution of 10.6 ml (82.3 mmol) of methylthioacetic acid ethyl ester in 30 ml of dichloromethane is added dropwise thereto. The mixture is stirred for a further 1 hour at -65° and then a solution of 11.5 ml (82.3 mmol) of triethylamine is added dropwise thereto. The mixture is allowed to rise to room temperature, then washed with a small amount of water, dried over sodium sulfate, filtered and concentrated by evaporation. The evaporation residue is taken up in 250 ml of diethyl ether; 30 ml of 2N hydrochloric acid are added and the mixture is stirred at room temperature for 16 hours. The red precipitate is filtered off, washed with diethyl ether and dried. 8.48 g (40% of theon. 1) of 6-chloro-3-methylthio-4-nitro-quinolin-2-one having a melting point of 213° (decorap.) are obtained.

Workup

  1. stirringThe mixture is stirred for a further 1 hour at -65°
  2. customto rise to room temperature
  3. washwashed with a small amount of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. addition30 ml of 2N hydrochloric acid are added
  8. stirringthe mixture is stirred at room temperature for 16 hours
  9. filtrationThe red precipitate is filtered off
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-3ebbc2fbc5194be2a669f26f3b500cb1
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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