Hydrochloric Acid → HCID 22674170, compound

HRID 1005706Notes

Reaction equation

HRID 1005706 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([F:16])([F:15])[F:14])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:15][C:13]([F:16])([F:14])[C:6]1[C:5]2[C:10](=[CH:11][C:2]([NH:1][S:24]([C:21]3[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=3)(=[O:26])=[O:25])=[CH:3][CH:4]=2)[O:9][C:8](=[O:12])[CH:7]=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

Procedure

To a solution of 7-amino-4-trifluoromethylcoumarin (200 mg, 0.87 mmol) and 4-dimethylaminopyridine (1 mg) in pyridine (3 ml) was added 4-chlorobenzenesulfonyl chloride (203 mg, 0.96 mmol), followed by stirring at 70 degrees for 50 minutes. To the reaction mixture was added 2 N hydrochloric acid, 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-6b1f44a7ca3b47a69e6d37c60e7a0c3d
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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