3,5-Dimethyl-1-benzothiophene-2-sulfonyl chloride → HCID 178423570, compound

HRID 589702Notes

Reaction equation

HRID 589702 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1.[CH3:13][C:14]1[C:18]2[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=2[S:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:13][C:14]1[C:18]2[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=2[S:16][C:15]=1[S:24]([NH:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:5]2[NH:1][N:2]=[N:3][N:4]=2)[CH:7]=1)(=[O:25])=[O:26]

Participants

4

Reactant 2

HCID 220414653,5-Dimethyl-1-benzothiophene-2-sulfonyl chloride2×HCID 178507542HCID 178507542, compound

Product 1

HCID 178423570HCID 178423570, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1H-tetrazol-5-yl)-phenylamine (161 mg, 10 mmol) in dry CH2Cl2 (10 mL) pyridine (0.5 mL) and 3,5-dimethyl-benzothiophene-2-sulfonyl chloride (Intermediate 13) (260 mg, 10 mmol) were added. The mixture was stirred for 4 h and then concentrated in vacuo. The product was purified by column chromatography on silica gel (eluent: 2 to 15% MeOH in CHCl3) affording 104 mg (27%) of the title compound. 1H NMR (DMSO-d6) δ ppm 2.40 (s, 3H) 2.52 (s, 3H) 7.29 (d, 1H) 7.35 (d, 1H) 7.42 (t, 1H) 7.70 (m, 2H) 7.85 (d, 1H) 7.92 (s, 1H). MS (ESI+) calcd for C17H15N5O2S2 385.066716, found 385.065826.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was purified by column chromatography on silica gel (eluent: 2 to 15% MeOH in CHCl3)

Sources & evidence

ORD record
ord-38c3572b8ab94f5b8c356d477fe6e73f
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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