Benzenesulfonamide → HCID 15636923, compound

HRID 1769955Notes

Reaction equation

HRID 1769955 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](C1C=CC([C:20]2[C:28]([CH2:29][C@H:30]3[C@@H:35]([OH:36])[C:34]4[CH:37]=[C:38]([O:41][CH2:42][C:43]5[S:44][C:45]6[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:46]=6[N:47]=5)[CH:39]=[CH:40][C:33]=4[O:32][CH2:31]3)=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([O-])=[O:23])=CC=1)([O-])=O.[H-].[Na+]>>[F:52][C:49]1[CH:50]=[CH:51][C:45]2[S:44][C:43]([CH2:42][O:41][C:38]3[CH:39]=[CH:40][C:33]4[O:32][CH2:31][C@@H:30]([CH2:29][C:28]5[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=5)[C:22]([NH:10][S:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:9])=[O:8])=[O:23])[C@@H:35]([OH:36])[C:34]=4[CH:37]=3)=[N:47][C:46]=2[CH:48]=1

Participants

4

Reactant 3

HCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 67704692HCID 67704692, compound

Product 1

HCID 15636923HCID 15636923, compound

Procedure

Synthesis was carried out as in example 1, but using 4.4 grams benzene sulfonamide instead of methane sulfonamide, and using 2.4 grams optically pure (-) cis-4-nitrophenyl-3-[[6-[(5-fluoro-2-benzothiazolyl)methoxy]-3,4-dihydro-4-hydroxy-2H-1-benzopyran-3-yl]methyl]benzoate and 628 milligrams sodium hydride. There was obtained 1.02 grams of product, m.p. 161°-162° C. αD =-30° ; c =0.005 in tetrahydrofuran.

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-737dd5b006e14ce7beda228cedd3f4ff
Source dataset
uspto-grants-1995_01
Patent number
US05384318

Reaction notes

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