Hydrochloric Acid → HCID 68587975, compound

HRID 2070235Notes

Reaction equation

HRID 2070235 reaction equation
O.O.[Sn](Cl)Cl.Cl.[C:7]([C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][CH:31]=1)[O:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:18]([N+:25]([O-])=O)=[C:17]([CH3:28])[CH:16]=1)([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][CH:31]=1)[O:14][C:15]1[C:20]([C:21]([F:24])([F:22])[F:23])=[CH:19][C:18]([NH2:25])=[C:17]([CH3:28])[CH:16]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 68587480HCID 68587480, compound

Product 1

HCID 68587975HCID 68587975, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Initially, at room temperature, 37.55 g (166.41 mmol) of tin(II) chloride dihydrate and then, with ice-cooling and slowly, 100 ml of concentrated hydrochloric acid are added to a solution of 19.60 g (55.47 mmol) of 4-(3-tertbutylphenoxy)-5-trifluoromethyl-2-methylnitrobenzene in 100 ml of methanol. The mixture is heated under reflux for 4 h, cooled to room temperature, concentrated, water is added and the residue is filtered off and dried under reduced pressure. The crude product is purified by column chromatography. (13.2 g, purity 86%, yield 63.5%, log P (pH 2.3)=4.67).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 h
  3. concentrationconcentrated
  4. additionwater is added
  5. filtrationthe residue is filtered off
  6. customdried under reduced pressure
  7. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-5a3950328df34ec788f42cfa1303a1ea
Source dataset
uspto-grants-2012_10
Patent number
US08299301B2

Reaction notes

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