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

HRID 1846872Notes

Reaction equation

HRID 1846872 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][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.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:22]2[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=2)(=[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 73974-Toluenesulfonyl chlorideHCID 215247532-Aminomethyl-5-benzyloxy-pyran-4-oneHCID 86725690N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Product 1

HCID 86725730N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-4-methyl-benzenesulfonamideYield 57.1%

Procedure

N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-4-methyl-benzenesulfonamide (7-06) (20.0 g, 57.08%) was synthesized as a light brown solid from 2-aminomethyl-5-benzyloxy-pyran-4-one (5) (21.0 g, 90.90 mmol) and 4-methyl-benzenesulfonyl chloride (6-06) (20.7 g, 109.09 mmol) following the procedure described for N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (7-01).

Sources & evidence

ORD record
ord-e9adf8da5d584f118f58dd4dd04f19c2
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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