Oxalyl chloride → 3,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenolchloride

HRID 330636Notes

Reaction equation

HRID 330636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([C:13]2[N:17]([CH:18]([CH3:20])[CH3:19])[N:16]=[N:15][N:14]=2)[C:10](O)=[O:11])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:31])=O>C(Cl)Cl>[Cl-:31].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([C:13]2[N:17]([CH:18]([CH3:20])[CH3:19])[N:16]=[N:15][N:14]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 147238703,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenoic acid

Product 1

HCID 199862413,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenolchloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the dried acid prepared in Step A in 20 mL of dry methylene chloride at room temperature was treated with 4 mL of oxalyl chloride (redistilled over CaH2). The mixture was refluxed under an argon atmosphere for two hours forming a light brownish solution. Most of the volatile solvents were evaporated under reduced pressure and the last traces of oxalyl chloride were removed under high vacuum (0.01 mmHg) at room temperature for 12 hours to give the title compound.

Workup

  1. temperatureThe mixture was refluxed under an argon atmosphere for two hours
  2. customforming a light brownish solution
  3. customMost of the volatile solvents were evaporated under reduced pressure
  4. customthe last traces of oxalyl chloride were removed under high vacuum (0.01 mmHg) at room temperature for 12 hours

Sources & evidence

ORD record
ord-9780c127e8214836b9ec959cf29ffdfa
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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