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

HRID 2260484Notes

Reaction equation

HRID 2260484 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 P2Os 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. customdried under vacuum over P2Os

Sources & evidence

ORD record
ord-9c5713db24dd43cab726d09c36db8578
Source dataset
uspto-grants-1995_12
Patent number
US05478811

Reaction notes

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