5-Chlorothiophene-2-sulfonyl chloride → HCID 24987865, compound

HRID 1170117Notes

Reaction equation

HRID 1170117 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([NH2:19])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.[Cl:20][C:21]1[S:25][C:24]([S:26](Cl)(=[O:28])=[O:27])=[CH:23][CH:22]=1>N1C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[NH:19][S:26]([C:24]3[S:25][C:21]([Cl:20])=[CH:22][CH:23]=3)(=[O:28])=[O:27])[N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 44217679HCID 44217679, compound

Product 1

HCID 24987865HCID 24987865, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N2-(5-Methyl-furan-2-ylmethyl)-quinoline-2,5-diamine (200 mg, 0.791 mmol) was dissolved in 2 mL pyridine and 5-chlorothiophene-2-sulfonylchloride (175 mg, 0.806 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of 50 mL water and 1.2 mL acetic acid. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). The title compound was obtained as a brown solid (192 mg, 56%), MS: m/e=434.3 (M+H+).

Workup

  1. customThe reaction mixture was quenched by addition of 50 mL water and 1.2 mL acetic acid
  2. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record
ord-a1f20ba32e734102ad30725376692a65
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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