Water → 4-(Morpholine-4-sulfonyl)benzoic acid

HRID 861302Notes

Reaction equation

HRID 861302 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.Cl[S:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)(=[O:19])=[O:18].O>C1COCC1>[N:10]1([S:17]([C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 5594164-(Morpholine-4-sulfonyl)benzoic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diisopropylethylamine (1.76 g, 13.6 mmol, 2.37 ml) and morpholine (1.98 g, 22.7 mmol, 1.98 ml) in THF (40 ml) was added, dropwise over 0.5 h, a solution of 4-(chlorosulfonyl)benzoic acid (2.50 g, 11.3 mmol) in THF (17 ml). After stirring at room temperature for 18 h the reaction was poured into H2O (150 ml) and washed with EtOAc. The aqueous layer was acidified (pH 1) with concentrated HCl, and the precipitate collected, washed with cold H2O, and dried under vacuum over P2O5 to give 2.68 g (87%) of 4-(4-morpholinylsulfonyl)-benzoic acid as an off-white solid.

Workup

  1. washwashed with EtOAc
  2. customthe precipitate collected
  3. washwashed with cold H2O
  4. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-3ee68e51c9ac480383b0050d0b0babcf
Source dataset
uspto-grants-1998_02
Patent number
US05714470

Reaction notes

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