N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide → 3-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide

HRID 1846865Notes

Reaction equation

HRID 1846865 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][CH:23]=[C:22]([Cl:26])[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:22]1[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][CH:23]=1

Participants

3

Reactant 2

HCID 86725691N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideHCID 86725722N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-3-chloro-benzenesulfonamide

Product 1

HCID 867257233-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamideYield 71.83%

Procedure

3-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (8-05) (14.0 g, 71.83%) was synthesized as a brown solid from N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-3-chloro-benzenesulfonamide (7-05) (25.0 g, 61.73 mmol) following the procedure described for N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (8-01).

Sources & evidence

ORD record
ord-b79ba2b70a624f6ca800f0907ab2bc91
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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