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Sulfuric Acid → ethyl 3,3-bis(4-fluorophenyl)-2-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-2-propenoate

HRID 974459
Notes
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Reaction equation

HRID 974459 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:9]([C:15]2[NH:19][N:18]=[N:17][N:16]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH3:27][C:28](=[CH2:30])[CH3:29].OS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([C:28]([CH3:30])([CH3:29])[CH3:27])[N:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 178470939HCID 178470939, compound

Product 1

HCID 14723818ethyl 3,3-bis(4-fluorophenyl)-2-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-2-propenoateYield 67.8%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Conditions

Temperature
-50 °C

Procedure

To a stirred suspension of 10 g of ethyl 3,3-bis(4-fluorophenyl)-2-(1H-tetrazol-5-yl)-2-propenoate in 250 mL dry diethyl ether cooled at -50° C. was slowly added 60 mL of liquid isobutylene (previously condensed from gaseous material in a dry ice-alcohol bath). With continued stirring and cooling, 50 mL of concentrated H2SO4 was added slowly and carefully. The mixture was then sealed in a stainless steel Parr container and stirred at -30° C. for 40 hours. After releasing the pressure, the mixture was added slowly and carefully to excess saturated NaHCO3 solution. The aqueous mixture was extracted with diethyl ether, dried over Na2SO4 and concentrated in vacuo to give 7.8 g (67.8%) of the title compound, m.p. 143°-144° C.

Workup

  1. custompreviously condensed from gaseous material in a dry ice-alcohol bath)
  2. temperaturecooling
  3. stirringstirred at -30° C. for 40 hours
  4. extractionThe aqueous mixture was extracted with diethyl ether
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67788b5eb50d46e1a2682c57ebc000df
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05068346

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes