HCID 58136914, compound → HCID 58136890, compound

HRID 1258521Notes

Reaction equation

HRID 1258521 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13]=[C:14]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:15]=1)[C:7](N(OC)C)=[O:8])[CH3:2].[CH3:22][Mg]Br>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7](=[O:8])[CH3:22])[CH:13]=[C:14]([S:16]([F:21])([F:17])([F:18])([F:19])[F:20])[CH:15]=1)[CH3:2]

Participants

4

Reactant 2

HCID 58136914HCID 58136914, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58136890HCID 58136890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Ethoxy-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (2.6 g) was dissolved in THF (60 ml). After cooling to 0° C., methylmagnesium bromide (6.46 ml, 3 M in ether) was added dropwise. Thereafter, the cooling bath was removed and stirring was continued at RT. After 1 h, the mixture was acidified with 1N hydrochloric acid, admixed with water and extracted by shaking twice with EA. The EA phases were dried over magnesium sulfate, filtered and concentrated. 2.25 g of the title compound were obtained.

Workup

  1. customThereafter, the cooling bath was removed
  2. customwas continued at RT
  3. extractionextracted
  4. stirringby shaking twice with EA
  5. dry with materialThe EA phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-909354291b9a4cbd984cf6dcd70e654e
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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