Oxalyl chloride → HCID 19986228, compound

HRID 974448Notes

Reaction equation

HRID 974448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][N:14]=2)[C:10](O)=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][N:14]=2)[CH2:10][Cl:29])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 14539524HCID 14539524, compound

Product 1

HCID 19986228HCID 19986228, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of dry (0.1 mmHg at 80° C.) 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)2-propenoic acid 3.8 g (11.0 mmoles) in 20 mL of dry methylene chloride was added 4 mL (46.0 mmoles) of purified oxalyl chloride (redistilled over CaH2) in one single portion. The reaction mixture was warmed gradually to reflux temperature for two hours. The mixture was evaporated under reduced pressure to remove volatile solvent, then excess oxalyl chloride was removed under vacuum (20 mmHg) at ambient temperature for 2 hours and under high vacuum (0.1 mmHg) at 50° C. for 16 hours to give the title compound.

Workup

  1. temperatureThe reaction mixture was warmed gradually
  2. temperatureto reflux temperature for two hours
  3. customThe mixture was evaporated under reduced pressure
  4. customto remove volatile solvent
  5. customexcess oxalyl chloride was removed under vacuum (20 mmHg) at ambient temperature for 2 hours and under high vacuum (0.1 mmHg) at 50° C. for 16 hours

Sources & evidence

ORD record
ord-f5dc85c4bcf74a619e8411fe1d4c30ad
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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