Methanesulfonyl chloride → HCID 86608971, compound

HRID 1715321Notes

Reaction equation

HRID 1715321 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([NH:10][C:11](=[O:31])[CH:12]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=1)[C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])([CH2:8][CH3:9])[CH3:7]>N1C=CC=CC=1>[CH:6]([NH:10][C:11]([CH:12]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:29])([F:30])[F:28])[CH:20]=1)[C:13]([CH3:16])([CH3:17])[CH2:14][O:15][S:2]([CH3:1])(=[O:4])=[O:3])=[O:31])([CH2:8][CH3:9])[CH3:7]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68508938HCID 68508938, compound

Product 1

HCID 86608971HCID 86608971, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
2.5 °C

Procedure

Methanesulfonyl chloride (36.45 g, 318 mmol) was added in one portion to a cold (0-5° C.) sol'n of the N-sec-butyl-2-(4-cyano-3-trifluoromethyl phenoxy)-4-hydroxy-3,3-dimethylbutyramide (5, 79.0 g, 212 mmol) in 200 mL pyridine. The reaction mixture was stirred at 0-5° C. for 5 h. The reaction was quenched with 800 mL sat'd aq. NH4Cl and extracted with 1000 mL CH2Cl2. The organic phase was washed with 2N aq. HCl (3×300 mL) and then half sat'd aq. NaCl (3×300 mL). The organic was conc'd under vac (35-40° C.) to an amber gum.

Workup

  1. customThe reaction was quenched with 800 mL
  2. extractionextracted with 1000 mL CH2Cl2
  3. washThe organic phase was washed with 2N aq. HCl (3×300 mL)
  4. customorganic was conc'd under vac (35-40° C.) to an amber gum

Sources & evidence

ORD record
ord-f86a7dde619f44178e98fbcf842f9bf0
Source dataset
uspto-grants-2010_09
Patent number
US07799823B2

Reaction notes

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