Sulfuric Acid → HCID 72312730, compound

HRID 1161371Notes

Reaction equation

HRID 1161371 reaction equation
N1C(C)=CC(C)=CC=1C.Cl[C:11]([O:13][CH3:14])=[O:12].[CH3:15][S:16][C:17](=[NH:39])[C:18](=[N:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1)[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=1[F:29].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:14][O:13][C:11](=[O:12])[N:39]=[C:17]([S:16][CH3:15])[C:18](=[N:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1)[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=1[F:29]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6586Methyl chloroformateHCID 79532,4,6-TrimethylpyridineHCID 59517045HCID 59517045, compound

Product 1

HCID 72312730HCID 72312730, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

After adding 2.97 ml of 2,4,6-collidine and 1.74 ml of methyl chloroformate to a solution of 2.01 g of 2-(4-cyanophenylimino)-2-(2-fluoro-3,5-dimethoxyphenyl)thioacetimidic acid methyl ester in 80 ml of toluene, the mixture was stirred at 85° C. for 20 hours under a nitrogen atmosphere. After cooling the reaction mixture, 400 ml of ethyl acetate and 200 ml of a 2% aqueous sulfuric acid solution were added and the organic layer was washed with 300 ml of water and 300 ml of saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate (3:2)) to give the title compound (1.89 g) as a light yellow solid.

Workup

  1. additionwere added
  2. washthe organic layer was washed with 300 ml of water and 300 ml of saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate (3:2))

Sources & evidence

ORD record
ord-6bae17e8ab674faf90db9130a2221801
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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