Water → HCID 67210797, compound

HRID 1179113Notes

Reaction equation

HRID 1179113 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[C:17]=2[N:18]=1.O>Cl>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[O:15][C:16]2[C:17](=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=2)[N:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24287Tin tetrachlorideHCID 67210867HCID 67210867, compound

Product 1

HCID 67210797HCID 67210797, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

14.3 g (63.5 mmol; 5 eq.) of tin chloride is added to a solution of 3.5 g (12.7 mmol) of 2-(2,6-difluorophenyl)-4-nitro-1,3-benzoxazole in 60 ml of concentrated hydrochloric acid. The mixture is stirred for 2 hours at 60° C., then, after returning to ambient temperature and the addition of 100 ml of water, is neutralized by a 50% aqueous solution of soda. The precipitate formed is filtered on a Celite bed and washed with ethanol. The resulting solution is concentrated under reduced pressure, then the desired product is extracted 3 times with 50 ml of ethyl acetate. The organic phases are combined, washed twice with 30 ml of a saturated solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The 2-(2,6-difluorophenyl)-1,3-benzoxazol-4-amine is used without other purification in the following stage.

Workup

  1. customafter returning to ambient temperature
  2. customThe precipitate formed
  3. filtrationis filtered on a Celite bed
  4. washwashed with ethanol
  5. concentrationThe resulting solution is concentrated under reduced pressure
  6. extractionthe desired product is extracted 3 times with 50 ml of ethyl acetate
  7. washwashed twice with 30 ml of a saturated solution of sodium chloride
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe 2-(2,6-difluorophenyl)-1,3-benzoxazol-4-amine is used without other purification in the following stage

Sources & evidence

ORD record
ord-3c7484dfba304b559fe95501692917c0
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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