Diisopropylethylamine → HCID 11376023, compound

HRID 606273Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:20](Cl)(=[O:22])=[O:21])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[Cl:18].CCN(C(C)C)C(C)C.[CH:33]([O:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1)([CH3:35])[CH3:34]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:20]([NH:41][C:40]2[CH:39]=[CH:38][C:37]([O:36][CH:33]([CH3:35])[CH3:34])=[CH:43][CH:42]=2)(=[O:22])=[O:21])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[Cl:18]

Participants

Conditions

Temperature: 40 °C

Procedure

To 100 mg of 3,5-Dichloro-4-(2-Chloro-4-Nitrophenoxy)Benzene-1-Sulfonyl Chloride (0.23 m.mol) was added 0.2 ml of DIEA, 5 ml of dichloromethane and 150 mg of 4-isopropoxyaniline. The mixture was maintained at 40° C. for 4 hours. The solvent was evaporated and the residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous Na2SO4 and the solvent evaporated. The residue as purified using radial silica-gel chromatography using 1:4 ethyl acetate:hexane as solvent. The purity of the product by LC/MS was 97.19%. M−1 (530) was seen in the mass spectrum. The yield of the product was 80.3 mg or 63% yield.

Workup

customThe solvent was evaporated
dissolutionthe residue dissolved in ethyl acetate
washwashed with water and brine
dry with materialThe organic layer was dried over anhydrous Na2SO4
customthe solvent evaporated
customThe residue as purified

Sources & evidence

ORD record: ord-8dedc6aaf12146a6a4052dd271b8421d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915293B2

Reaction notes

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