Water → HCID 67210867, compound

HRID 1179112Notes

Reaction equation

HRID 1179112 reaction equation
B(O)(O)O.[NH2:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:15].[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:18]=1[C:19](O)=O.O>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:18]=1[C:19]1[O:15][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=2[N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7628Boric AcidHCID 97962,6-Difluorobenzoic acidHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 67210867HCID 67210867, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2 g (32.4 mmol; 1 eq.) of boric acid is added to a solution of 5 g (32.4 mmol) of 2-amino-3-nitrophenol and 5.12 g (32.4 mmol; 1 eq.) of 2,6-difluorobenzoic acid in 50 ml of xylene. The mixture is heated under reflux of the xylene for 8 hours with elimination of the water formed by a Dean-Stark apparatus. After returning to ambient temperature, the reaction medium is diluted by 100 ml of ethyl acetate and neutralized by a 10% aqueous solution of soda. The organic phase is washed 3 times with 50 ml of water then with a saturated solution of NaCl before being dried over sodium sulphate, filtered and concentrated under reduced pressure. The 2-(2,6-difluorophenyl)-4-nitro-1,3-benzoxazole is used without other purification in the following stage.

Workup

  1. temperatureThe mixture is heated
  2. customformed by a Dean-Stark apparatus
  3. customAfter returning to ambient temperature
  4. washThe organic phase is washed 3 times with 50 ml of water
  5. dry with materialwith a saturated solution of NaCl before being dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe 2-(2,6-difluorophenyl)-4-nitro-1,3-benzoxazole is used without other purification in the following stage

Sources & evidence

ORD record
ord-34e055c8411443369cc5de0188fd6183
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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