Phenol → HCID 66799888, compound

HRID 589779Notes

Reaction equation

HRID 589779 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1.[C:25]1(O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([O:19][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid2×

Product 1

HCID 66799888HCID 66799888, compoundYield 74%

Procedure

The product was prepared from 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (21 mg, 0.055 mmol) (Intermediate 19) and phenol (9.4 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107. The title compound was obtained in 74% yield (18.7 mg). 1H NMR (500 MHz, CDCl3) δ ppm 2.50 (s, 3 H) 7.06 (s, 1 H) 7.10-7.15 (m, 2 H) 7.25-7.29 (m, 1 H) 7.39-7.44 (m, 2 H) 7.44 (dd, J=8.10, 7.70 Hz, 1 H) 7.44 (dd, J=8.65, 2.02 Hz, 1 H) 7.51 (ddd, J=8.10, 2.34, 1.15 Hz, 1 H) 7.72 (dd, J=8.65, 0.57 Hz, 1 H) 7.73 (dd, J=2.02, 0.57 Hz, 1 H) 7.86 (dd, J=2.34, 1.58 Hz, 1H) 7.99 (ddd, J=7.70, 1.58, 1.15 Hz, 1 H). MS (ESI+) m/z 458 [M+H]+.

Sources & evidence

ORD record
ord-7a4c5fbc7a9f4aabb7797a9bb4e2a171
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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