Diisopropylethylamine → 2-Chlorobenzene-1-sulfonic acid

HRID 482092Notes

Reaction equation

HRID 482092 reaction equation
N1CCCC(COC2C=C([O:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(=[O:19])=[O:18])C=C(C)C=2)C1.C(N(CC)C(C)C)(C)C.NN=CS(O)(=O)=O>CN(C=O)C>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([OH:19])(=[O:18])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 536550322-Chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester

Product 1

HCID 135314532-Chlorobenzene-1-sulfonic acidYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester (396 mg, 1.0 mmol), as prepared in the preceding step, in DMF (10 mL) containing N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) was stirred at room temperature overnight. The DMF was removed in vacuo and the residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3) to give the title compound as a white foam (159 mg, 36%). 1H-NMR (300 MHz, CDCl3) δ 1.45-1.92 (m, 4H), 2.11 (m, 1H), 2.23 (s, 3H), 3.07 (m, 2H), 3.81 (d, 2H), 3.92 (m, 2H), 6.50 (s, 2H), 6.61 (s, 1H), 7.24 (bs, 3H), 7.40 (m, 1H), 7.63 (m, 2H), 7.95 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H24N3 O4SCl: 438.1 (M+H), 460.1 (M+Na), Found: 438.5, 460.5.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3)

Sources & evidence

ORD record
ord-c3554de2a0044adfa27dfbcc7fab88a2
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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