Sodium Sulfate → Cyclaniliprole

HRID 1641459Notes

Reaction equation

HRID 1641459 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:8][C:9]1[C:22]([Br:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:10]=1[C:11]([NH:13][CH:14]([CH:16]1[CH2:18][CH2:17]1)[CH3:15])=[O:12].[Br:25][C:26]1[CH:30]=[C:29]([C:31](OC2C=CC=CC=2)=[O:32])[N:28]([C:40]2[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][N:41]=2)[N:27]=1.CC(C)([O-])C.[K+]>O.CS(C)=O>[Br:25][C:26]1[CH:30]=[C:29]([C:31]([NH:8][C:9]2[C:10]([C:11](=[O:12])[NH:13][CH:14]([CH:16]3[CH2:18][CH2:17]3)[CH3:15])=[CH:19][C:20]([Cl:24])=[CH:21][C:22]=2[Br:23])=[O:32])[N:28]([C:40]2[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][N:41]=2)[N:27]=1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 23665647Potassium tert-butoxideHCID 667362892-amino-3-bromo-5-chloro-N-(1-cyclopropylethyl)benzamideHCID 66737070phenyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 24822142CyclaniliproleYield 55.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

0.45 g of anhydrous sodium sulfate was added to a mixed solution comprising 0.23 g of 2-amino-3-bromo-5-chloro-N-(1-cyclopropylethyl)benzamide, 0.27 g of phenyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate and 5 ml of dimethyl sulfoxide at room temperature, and 0.16 g of potassium tert-butoxide was added, followed by reaction for one hour. Then, the reaction liquid was slowly added to water. The mixed liquid was subjected to extraction with ethyl acetate, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 4/6) to obtain 0.24 g of the desired product.

Workup

  1. customat room temperature
  2. customfollowed by reaction for one hour
  3. customThen, the reaction liquid
  4. extractionThe mixed liquid was subjected to extraction with ethyl acetate
  5. washthe organic layer was washed with a sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 4/6)

Sources & evidence

ORD record
ord-eb943b310dc9481fb0f9b9ea052529e9
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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