N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide → 4-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide

HRID 1846881Notes

Reaction equation

HRID 1846881 reaction equation
C([O:8][C:9]1[C:10](=[O:27])[CH:11]=[C:12]([CH2:15][NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[O:13][CH:14]=1)C1C=CC=CC=1.OC1C(=O)C=C(CNS(C2C=CC=CC=2)(=O)=O)OC=1>>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([S:17]([NH:16][CH2:15][C:12]2[O:13][CH:14]=[C:9]([OH:8])[C:10](=[O:27])[CH:11]=2)(=[O:19])=[O:18])=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 86725691N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideHCID 86725737N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamide

Product 1

HCID 867257384-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamideYield 89.8%

Procedure

4-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (8-07) (14.0 g, 89.79%) was synthesized as a light brown solid from N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamide (7-07) (20.0 g, 49.38 mmol) following the procedure described for N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (8-01).

Sources & evidence

ORD record
ord-17f9237808aa444490d9378f638839fd
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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