o-Toluenesulfonyl chloride → N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-2-methyl-benzenesulfonamide

HRID 1846840Notes

Reaction equation

HRID 1846840 reaction equation
[NH2:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26].C(OC1C(=O)C=C(CNS(C2C=CC=CC=2)(=O)=O)OC=1)C1C=CC=CC=1>>[CH2:11]([O:10][C:6]1[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][NH:1][S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH3:18])(=[O:27])=[O:26])[O:4][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 8623o-Toluenesulfonyl chlorideHCID 215247532-Aminomethyl-5-benzyloxy-pyran-4-oneHCID 86725690N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Product 1

HCID 86725698N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-2-methyl-benzenesulfonamideYield 64.32%

Procedure

N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-2-methyl-benzenesulfonamide (7-02) (22.0 g, 64.32%) was synthesized as a light brown solid from 2-aminomethyl-5-benzyloxy-pyran-4-one (5) (20.5 g, 88.74 mmol) and 2-methyl-benzenesulfonyl chloride (6-02) (20.23 g, 106.49 mmol) following the procedure described for N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (7-01).

Sources & evidence

ORD record
ord-a469a7d75e1e4bfd9251676225b48533
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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