Water → 1-(2-Methoxy-4-(trifluoromethyl)phenyl)phthalazine-6-sulfonyl chloride

HRID 1473403Notes

Reaction equation

HRID 1473403 reaction equation
C(S[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[O:29][CH3:30])=[N:14][N:13]=[CH:12]2)C1C=CC=CC=1.O.[Cl:32]N1C(C)(C)C(=O)N(Cl)C1=O.[O-:43][S:44]([O-:47])(=O)=O.[Mg+2]>CC#N.C(O)(=O)C.C(Cl)Cl>[CH3:30][O:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:28])[F:27])[CH:23]=[CH:24][C:19]=1[C:15]1[C:16]2[C:11](=[CH:10][C:9]([S:44]([Cl:32])(=[O:47])=[O:43])=[CH:18][CH:17]=2)[CH:12]=[N:13][N:14]=1

Participants

8

Reactant 4

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 24083Sulfuric acid magnesium salt (1:1)HCID 866874486-(Benzylthio)-1-(2-methoxy-4-(trifluoromethyl)phenyl)phthalazine

Product 1

HCID 866874491-(2-Methoxy-4-(trifluoromethyl)phenyl)phthalazine-6-sulfonyl chlorideYield 62.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(benzylthio)-1-(2-methoxy-4-(trifluoromethyl)phenyl)phthalazine 2 (0.340 g, 0.797 mmol) in 20 mL of MeCN, 0.75 mL of acetic acid, and 0.5 mL of water (20/0.75/0.5 ratio) was cooled to 0° C. and was treated with 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.314 g, 1.595 mmol). After stirring for one hour, LC/MS showed mostly product, so the reaction mixture was diluted with DCM and was treated with MgSO4. After stirring for 10 minutes, the reaction mixture was filtered and concentrated. Purification of the crude residue by silica gel column chromatography (0 to 40% EtOAc/heptane) gave 1-(2-methoxy-4-(trifluoromethyl)phenyl)phthalazine-6-sulfonyl chloride (0.200 g, 0.497 mmol, 62.3% yield).

Workup

  1. stirringAfter stirring for 10 minutes
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography (0 to 40% EtOAc/heptane)

Sources & evidence

ORD record
ord-9551b58396704260982528961a5df666
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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