Trimethylsilylacetylene → 5-Ethynylthiophene-2-sulfonamide

HRID 1293755Notes

Reaction equation

HRID 1293755 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1.C[Si]([C:15]#[CH:16])(C)C>>[C:15]([C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1)#[CH:16]

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 12413045-Bromo-2-thiophenesulfonamide

Product 1

HCID 860437955-Ethynylthiophene-2-sulfonamide

Procedure

Prepared from 5-bromo-thiophene-2-sulfonic acid amide (1.94 g, 8 mmol) and trimethylsilylacetylene (2.2 mL, 12 mmol) by applying in analogous manner the procedures described in example D.1 (method 1, steps 1–2). Obtained after chromatographic purification of the crude product (SiO2, 0–75% AcOEt/heptane) as a light brown solid (0.49 g, 33%). MS (ISP) 186.1 [(M−H)−]; mp 114–116° C.

Workup

  1. customObtained
  2. customafter chromatographic purification of the crude product (SiO2, 0–75% AcOEt/heptane) as a light brown solid (0.49 g, 33%)

Sources & evidence

ORD record
ord-1f6620eaf5fb4cec9290219b90a1ae39
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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