5-Amino-2-methoxyphenol → 1,3-Dichloro-2,4,6-trifluoro-5-[(3-hydroxy-4-methoxyphenyl)aminosulfonyl]benzene

HRID 1936200Notes

Reaction equation

HRID 1936200 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].[Cl:11][C:12]1[C:13]([F:25])=[C:14]([S:21](Cl)(=[O:23])=[O:22])[C:15]([F:20])=[C:16]([Cl:19])[C:17]=1[F:18]>>[Cl:11][C:12]1[C:13]([F:25])=[C:14]([S:21]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:2]([OH:1])[CH:3]=2)(=[O:23])=[O:22])[C:15]([F:20])=[C:16]([Cl:19])[C:17]=1[F:18]

Participants

3

Reactant 2

HCID 743145-Amino-2-methoxyphenolHCID 155506413,5-Dichloro-2,4,6-trifluorophenylsulfonyl chloride

Product 1

HCID 98658171,3-Dichloro-2,4,6-trifluoro-5-[(3-hydroxy-4-methoxyphenyl)aminosulfonyl]benzene

Procedure

The title compound was prepared in a manner similar to that described in Example 1 by replacing p-anisidine with 3-hydroxy-4-methoxyaniline and replacing 4-fluoro-3-nitrophenylsulfonyl chloride with 3,5-dichloro-2,4,6-trifluorophenylsulfonyl chloride (Example B). 1H-NMR (CDCl3): δ 6.88 (1H, br s), 6.7-6.8 (3H, m), 5.66 (1H, s), 3.85 (3H, s), MS(EI): 402 (15, M+), 401 (20), 138 (100). Anal. Calcd. for C13H8Cl2F3NO4S: C, 38.83; H, 2.00; N, 3.48; S, 7.97. Found: C, 38.66; H, 1.97; N, 3.39; S, 7.86.

Sources & evidence

ORD record
ord-442ede7dbe9a4e67a6b23c9ab1ba31ad
Source dataset
uspto-grants-2002_05
Patent number
US06388131B2

Reaction notes

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