Ethyl Acetate → HCID 54269281, compound

HRID 1612574Notes

Reaction equation

HRID 1612574 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)=[CH:4][C:3]=1[NH:20][CH:21]([CH3:24])[CH2:22][OH:23].[N:25]([O-])=O.[Na+].C(OCC)(=O)C>C(O)(=O)C.O>[Cl:14][C:13]1[C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]3[N:1]=[N:25][N:20]([CH:21]([CH3:24])[CH2:22][OH:23])[C:3]=3[CH:4]=2)=[N:10][N:11]([CH3:19])[C:12]=1[C:15]([F:18])([F:17])[F:16]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 19775925HCID 19775925, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 54269281HCID 54269281, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

The diamine obtained in Step C (1.08 g) was dissolved in glacial acetic acid (20 cm3) and water (2 cm3) and cooled to below 5° C. in an ice/salt bath. A solution of sodium nitrite (0.41 g, 5.9 mmol) in water (5 cm3) was added dropwise, at such a rate that the internal temperature was maintained below 5° C., and when the addition was complete the reaction mixture was stirred for 4 hours, during which it was allowed to warm to room temperature. The mixture was poured into ethyl acetate (100 cm3) and washed successively with water (2×100 cm3) and saturated aqueous sodium bicarbonate solution (100 cm3). The organic phase was dried (MgSO4), filtered and the filtrate evaporated under reduced pressure. The residue was further purified by flash column chromatography on silica gel, eluting with diethyl ether, to give compound 9, DL 2-[6-(4-chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy) benzotriazol-1-yl]-propan-1-ol (0.90 g) as an off white solid m.p. 153°-154° C.

Workup

  1. temperatureat such a rate that the internal temperature was maintained below 5° C.
  2. additionwhen the addition
  3. washwashed successively with water (2×100 cm3) and saturated aqueous sodium bicarbonate solution (100 cm3)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customThe residue was further purified by flash column chromatography on silica gel
  8. washeluting with diethyl ether

Sources & evidence

ORD record
ord-249ec7c8dc5541dbb93b357e70246264
Source dataset
uspto-grants-1993_03
Patent number
US05190574

Reaction notes

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