Water → 2,6-bis(1,1-dimethylethyl)-4-(N-methyl-N-[1-phenyl-1H-pyrazol-3-yl]amino)phenyl acetate

HRID 22277Notes

Reaction equation

HRID 22277 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([N:11]([CH3:23])[C:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:8]=[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[OH:28])([CH3:4])[CH3:3].C([Li])CCC.[C:34](Cl)(=[O:36])[CH3:35].O>O1CCCC1>[C:34]([O:28][C:6]1[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:10][C:9]([N:11]([CH3:23])[C:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][C:7]=1[C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 199279692,6-bis (1,1-dimethylethyl)-4-(N-methyl-N-[1-phenyl-1H-pyrazol-3-yl]amino)phenolHCID 178418339Butyllithium

Product 1

HCID 539630392,6-bis(1,1-dimethylethyl)-4-(N-methyl-N-[1-phenyl-1H-pyrazol-3-yl]amino)phenyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,6-bis (1,1-dimethylethyl)-4-(N-methyl-N-[1-phenyl-1H-pyrazol-3-yl]amino)phenol (0.6 g) in dry tetrahydrofuran (15 ml) at -78° under nitrogen was added butyl lithium (1.29 ml of 1.4M hexane solution). After 10 minutes acetyl chloride (0.2 ml) was added. The reaction was left for 16 hours, poured into water and extracted with ethyl acetate. Evaporation, and chromatography (silica, dichloromethane/hexane [1:1]) of the residue, followed by recrystallisation from hexane at -20° gave the title compound (0.35 g), mp 102°-103°.

Workup

  1. extractionextracted with ethyl acetate
  2. customEvaporation, and chromatography (silica, dichloromethane/hexane [1:1]) of the residue
  3. customfollowed by recrystallisation from hexane at -20°

Sources & evidence

ORD record
ord-e9d95f037bac4fd2890a41f03e527435
Source dataset
uspto-grants-1995_06
Patent number
US05428044

Reaction notes

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