Hydrochloric Acid → HCID 20033663, compound
Reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[S:15][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:13][C:12]=2[CH3:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:21][NH:22][CH3:23].[CH2:24]=[O:25].Cl>C(O)C>[CH3:21][N:22]([CH2:4][C:3]1[C:24]([OH:25])=[C:5]([S:8]([C:11]2[S:15][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:13][C:12]=2[CH3:20])(=[O:10])=[O:9])[CH:6]=[CH:7][CH:2]=1)[CH3:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 98 °C
Procedure
To 5-(4-hydroxyphenylsulfonyl)-4-methylthiophene-2-sulfonamide (2.0 g, 0.006 mol) in ethanol (10 ml) was added 40% aqueous dimethylamine (2.7 g, 0.024 mol) followed by 37% aqueous formaldehyde (0.59, 0.0072 mol). The solution was stirred in an oil bath (98° C.) for 161/2 hours. The solvent was removed in vacuo. The residual oil was taken up in ethyl acetate and extracted with dilute HCl. The HCl extract was basified with NaHCO3 and the product was extracted into ethyl acetate. The extract was washed with water, dried, filtered and concentrated in vacuo. This procedure gave a solid foam in 44% yield which was converted to the hydrochloride salt with ethanolic HCl. The white solid HCl salt melted at 262°-263° C. Purity and structure were confirmed by C, H, N analyses, HPLC and NMR.
Workup
- customThe solvent was removed in vacuo
- extractionextracted with dilute HCl
- extractionThe HCl extract
- extractionthe product was extracted into ethyl acetate
- washThe extract was washed with water
- customdried
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThis procedure gave a solid foam in 44% yield which
Sources & evidence
- ORD record
- ord-803bb1072de64e6292337357419c628c
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04847289
Reaction notes
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