Hydrochloric Acid → HCID 23221636, compound

HRID 612380Notes

Reaction equation

C[NH-].[Cl:3][C:4]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([S:18](Cl)(=[O:20])=[O:19])[CH:10]=[CH:11][C:12]=1[NH:13][S:14]([CH3:17])(=[O:16])=[O:15].ClC1C=C(Cl)C=CC=1OC1C=C(S(Cl)(=O)=O)C=C[C:36]=1[NH:37]S(C)(=O)=O.Cl.CN.[OH-].[Na+].Cl>O1CCOCC1>[CH3:36][NH:37][S:18]([C:9]1[CH:10]=[CH:11][C:12]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[C:7]([O:6][C:5]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:4]=2[Cl:3])[CH:8]=1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(2,4-Dichlorophenoxy)4-methylsulphonylaminobenzene-sulphonic acid chloride N-methylamide (HN-56203) 3-(2,4-dichlorophenoxy)-4-methylsulphonylaminobenzenesulphonic acid chloride (0.56 g, 1.3 mmol) was dissolved in dioxan (15 ml) and at 0° C. it was added dropwise to a solution of methylamine hydrochloride (1.18 g, 17 mmol) in 1N aqueous NaOH (15 ml, 15 mmol) and dioxan (20 ml). The mixture was stirred for 1 hour at 0° C., acidified with 1N HCl and extracted with ethyl acetate. The combined organic phases were dried over MgSO4 and the solvent was evaporated off. The residue was purified by chromatography (silica gel, CH2Cl2 /ethyl acetate 9/1). Yield: 0.25 g=45% 13C (100 MHz, CDCl3) δ 148.35, 146.21, 134.97, 132.03, 131.28, 131.16, 128.98, 127.15, 123.15, 123.12, 119.56, 113.81, 40.45, 29.18

Workup

extractionextracted with ethyl acetate
dry with materialThe combined organic phases were dried over MgSO4
customthe solvent was evaporated off
customThe residue was purified by chromatography (silica gel, CH2Cl2 /ethyl acetate 9/1)

Sources & evidence

ORD record: ord-af723933bade47a8a9662934b96094fe
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06004948

Reaction notes

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