P-Anisidine → HCID 12016873, compound

HRID 1936201Notes

Reaction equation

HRID 1936201 reaction equation
[Br:1][C:2]1[C:3]([F:14])=[C:4]([F:13])[C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[Br:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[CH:18][C:17]=1[S:25](Cl)(=[O:27])=[O:26].COC1C=CC(N)=CC=1.[OH:38][C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[NH2:42]>>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([NH:42][C:41]2[CH:43]=[CH:44][C:45]([O:46][CH3:47])=[C:39]([OH:38])[CH:40]=2)(=[O:10])=[O:9])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14].[Br:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[CH:18][C:17]=1[S:25]([NH:42][C:41]1[CH:43]=[CH:44][C:45]([O:46][CH3:47])=[C:39]([OH:38])[CH:40]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 743145-Amino-2-methoxyphenolHCID 12016869HCID 12016869, compoundHCID 12016870HCID 12016870, compound

Product 2

HCID 12016873HCID 12016873, compoundHCID 12016874HCID 12016874, compound

Procedure

1-Bromo-2,3,4-trifluoro-5-[(3-hydroxy-4-methoxyphenyl)aminosulfonyl]benzene (Example 12) and 1-Bromo-4,5,6-trifluoro-2-[(3-hydroxy-4-methoxyphenyl)aminosulfonyl]benzene (Example 13) were prepared in a manner similar to that described in Example 1 by replacing 4-fluoro-3-nitrophenylsulfonyl chloride with a mixture of 5-bromo-2,3,4-trifluorophenylsulfonyl chloride (Example D) and 2-bromo-3,4,5-trifluorophenylsulfonyl chloride (Example E) and replacing p-anisidine with 3-hydroxy-4-methoxyaniline. The two isomeric compounds were separated by column chromatography (silica gel; ethyl acetate:hexanes, 1:4). 1H-NMR (CDCl3): δ 7.79 (1H, m), 6.72-6.62 (4H, m), 5.65 (1H, s), 3.85 (3H, s).

Workup

  1. customThe two isomeric compounds were separated by column chromatography (silica gel; ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-62051455c44c4f7fad54645a0494b699
Source dataset
uspto-grants-2002_05
Patent number
US06388131B2

Reaction notes

Loading…