Hydrochloric Acid → HCID 22674170, compound

HRID 1173148Notes

Reaction equation

HRID 1173148 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([C:24]([F:27])([F:26])[F:25])=[CH:18][C:19](=[O:23])[O:20]2)=[CH:15][CH:14]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:27][C:24]([F:25])([F:26])[C:17]1[C:16]2[C:21](=[CH:22][C:13]([NH:12][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])=[CH:14][CH:15]=2)[O:20][C:19](=[O:23])[CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 1006417-Amino-4-(trifluoromethyl)coumarin

Product 1

HCID 22674170HCID 22674170, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

203 mg (0.96 mmol) of 4-chlorobenzenesulfonyl chloride was added to a pyridine solution (3 ml) containing 200 mg (0.87 mmol) of 7-amino-4-trifluoromethylcumarin and 1 mg of 4-dimethylaminopyridine, followed by stirring at 70° C. for 50 minutes. An aqueous 2 N hydrochloric acid was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated. The resulting residue was crystallized from ethyl acetate-diisopropyl ether, to give 253 mg of the title compound as a pale yellow solid.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-093d4ce45c7044148e65f7a54b2be59b
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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