Trimethylsilylacetylene → 5-Ethynylthiophene-2-sulfonamide

HRID 558646Notes

Reaction equation

HRID 558646 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-f981a49da84b4cf5b6cdad4992d0160b
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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