Methanol → HCID 89656313, compound

HRID 930945Notes

Reaction equation

HRID 930945 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[Br:7][C:8]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([N+:26]([O-:28])=[O:27])[CH:9]=1.CO>CN(C)C=O.ClCCl>[Br:7][C:8]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[CH:15][C:11]([C:12]([O:14][CH3:1])=[O:13])=[C:10]([N+:26]([O-:28])=[O:27])[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 89655907HCID 89655907, compound

Product 1

HCID 89656313HCID 89656313, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (1.4 mL, 16.6 mmol) was added dropwise to a 0° C. suspension of Example 324a (5.47 g, 14.6 mmol) and dichloromethane (65 mL). 3 drops dimethylformamide was added and the reaction mixture was stirred at ambient temperature for 2 hours. After cooling to 0° C., methanol (12 mL, 296 mmol) was added dropwise. The solution was stirred for 15 minutes at 0° C. and for 2.5 hours at ambient temperature. The solution was diluted with dichloromethane and was washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (5.42 g, 96% yield).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringThe solution was stirred for 15 minutes at 0° C. and for 2.5 hours at ambient temperature
  3. washwas washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-deeb67d4397746fb9545ecd1db913da1
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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