5-Methyl-1-benzothiophene-2-sulfonyl chloride → 5-Methyl-N-[3-(1H-tetrazol-5-yl)phenyl]-1-benzothiophene-2-sulfonamide

HRID 589708Notes

Reaction equation

HRID 589708 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[CH:7][C:6]=2[CH:14]=1.[NH2:15][C:16]1[CH:17]=[C:18]([C:22]2[NH:26][N:25]=[N:24][N:23]=2)[CH:19]=[CH:20][CH:21]=1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[NH:26][N:25]=[N:24][N:23]=4)[CH:17]=3)(=[O:12])=[O:11])=[CH:7][C:6]=2[CH:14]=1

Participants

3

Reactant 2

HCID 27947715-Methyl-1-benzothiophene-2-sulfonyl chlorideHCID 178507542HCID 178507542, compound

Product 1

HCID 1784235695-Methyl-N-[3-(1H-tetrazol-5-yl)phenyl]-1-benzothiophene-2-sulfonamideYield 25%

Procedure

The product was prepared according to General Procedure 1, described in Example 1, starting from 5-methyl-benzothiophene-2-sulfonyl chloride (30 mg, 0.12 mmol) and 5-(3-aminophenyl)tetrazole (20 mg, 0.12 mmol) giving the title compound as a white solid (11 mg, 25%). 1H NMR (400 MHz, MeOH-d4) δ ppm 2.40 (s, 3 H) 7.25-7.30 (m, 1 H) 7.34-7.40 (m, 1 H) 7.45 (t, J=7.91 Hz, 1 H) 7.62-7.65 (m, 1 H) 7.68-7.74 (m, 2 H) 7.78 (s, 1 H) 7.94 (t, J=1.88 Hz, 1 H). MS (ESI+) calcd for C16 H13N5O2S2 371.051066, found 371.050166.

Workup

  1. customThe product was prepared

Sources & evidence

ORD record
ord-8ba3050557f34657a7f3deed7e591306
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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