Hydrochloric Acid → HCID 19103277, compound

HRID 3778Notes

Reaction equation

HRID 3778 reaction equation
O[Li].O.[F:4][C:5]1([F:15])[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([NH2:14])[C:7]=2[O:6]1.[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[C:21]([C:28]([F:31])([F:30])[F:29])[C:20]=1Cl)([O-:18])=[O:17].Cl>CS(C)=O.O>[F:15][C:5]1([F:4])[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([NH:14][C:20]3[C:21]([C:28]([F:30])([F:31])[F:29])=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=3[N+:16]([O-:18])=[O:17])[C:7]=2[O:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-HCID 168937Lithium hydroxide, monohydrateHCID 27368912,2-Difluoro-1,3-dioxaindan-4-amine

Product 1

HCID 19103277HCID 19103277, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

20.8 g of LiOH.H2O are added at 0° C. to a solution of 24.5 g of 2,2-difluoro-4-amino-1,3-benzodioxole in 70 ml of dimethyl sulfoxide. The mixture is then stirred for 20 minutes. Subsequently, a solution of 38.3 g of 2,4-dinitro-6-trifluoromethylchlorobenzene in 70 ml of dimethyl sulfoxide is added, and the resultant reaction mixture is stirred at 0° C. for 20 minutes and then heated to room temperature. After 5 hours, the mixture is poured into 350 ml of water, acidified with dilute hydrochloric acid and extracted several times with diethyl ether. The combined ether phases are washed three times with a 5% solution of sodium carbonate and then with 5% hydrochloric acid and dried over sodium sulfate, and the solvent is evaporated off in vacuo. The residue comprises 51.6 g of orange-brown crystals which are recrystallised in toluene. Yield: 41.6 g; melting point: 144°-146° C.

Workup

  1. customthe resultant reaction mixture
  2. stirringis stirred at 0° C. for 20 minutes
  3. waitAfter 5 hours
  4. extractionextracted several times with diethyl ether
  5. washThe combined ether phases are washed three times with a 5% solution of sodium carbonate
  6. dry with materialwith 5% hydrochloric acid and dried over sodium sulfate
  7. customthe solvent is evaporated off in vacuo
  8. customare recrystallised in toluene

Sources & evidence

ORD record
ord-c71b9f3cdcad49d1b3a53a42a03aed7c
Source dataset
uspto-grants-1988_02
Patent number
US04722935

Reaction notes

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