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

HRID 1846849Notes

Reaction equation

HRID 1846849 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]=[CH:22][C:21]=2[Cl:26])(=[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:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([NH:16][CH2:15][C:12]1[O:13][CH:14]=[C:9]([OH:8])[C:10](=[O:27])[CH:11]=1)(=[O:18])=[O:19]

Participants

3

Reactant 2

HCID 86725691N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideHCID 86725707N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamide

Product 1

HCID 867257082-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamideYield 74%

Procedure

2-Chloro-N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (8-03) (15.0 g, crude) was synthesized as a light brown solid from N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamide (7-03) (26.0 g, 64.19 mmol) following the procedure described for N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (8-01).

Sources & evidence

ORD record
ord-19d8220306224f299449f70a86c905c2
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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