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N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide → N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamide

HRID 1846852
Notes
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Reaction equation

HRID 1846852 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])(=[O:21])=[O:20])[O:13][C:14]=1[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(=O)C=C(CNS(C2C=CC=CC=2)(=O)=O)OC=1C=O)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])(=[O:21])=[O:20])[O:13][C:14]=1[CH:15]=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 86725694N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideHCID 86725710N-(5-Benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamide

Product 1

HCID 86725711N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamideYield 85.1%

Procedure

N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamide (11-03) (2.8 g, 85.07%) was synthesized as a brown sticky solid from N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-2-chloro-benzenesulfonamide (10-03) (3.3 g, 7.58 mmol) following the procedure described for N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (11-01).

Sources & evidence

ORD record
ord-9e1b9266e586458e99ba4a8f02868a31
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952039B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes