tert-Butanol → [6-[3-(Trifluoromethyl)phenyl]-4-pyridazinyl]carbamic acid, 1,1-dimethylethyl ester

HRID 54648Notes

Reaction equation

HRID 54648 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[N:13][CH:12]=[C:11](C(O)=O)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.C([N:39]([CH2:42]C)CC)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[N:13][CH:12]=[C:11]([NH:39][C:42](=[O:27])[O:48][C:44]([CH3:47])([CH3:46])[CH3:45])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 152753066-[3-(Trifluoromethyl)phenyl]-4-pyridazinecarboxylic acid

Product 1

HCID 57320980[6-[3-(Trifluoromethyl)phenyl]-4-pyridazinyl]carbamic acid, 1,1-dimethylethyl ester

Procedure

6-[3-(trifluoromethyl)phenyl]-4-pyridazinecarboxylic acid (30 g, 0.112 mole, Compound No. 2), diphenylphosphorylazide (33.9 g, 0.123 mole) and triethylamine (17 g, 0.168 mole) were refluxed under N2 in t-butanol (250 mL) for 4 h. The mixture was then partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), filtered through silica gel and evaporated in vacuo to give a crude solid which can be utilized as is in the next step or chromatographed on a Prep-500 to give [6-[3-(trifluoromethyl)phenyl]-4-pyridazinyl]carbamic acid, 1,1-dimethylethyl ester (Compound No. 3) as a white solid which was recrystallized from cyclohexane/ethyl acetate.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered through silica gel
  4. customevaporated in vacuo
  5. customto give a crude solid which
  6. customchromatographed on a Prep-500

Sources & evidence

ORD record
ord-d99579c5e79e41538d158bbb21f99642
Source dataset
uspto-grants-1997_04
Patent number
US05623072

Reaction notes

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