HCID 59168801, compound → HCID 25065409, compound

HRID 1515966Notes

Reaction equation

HRID 1515966 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[C:8]([S:15]([NH2:18])(=[O:17])=[O:16])=[C:9]([N+:12]([O-])=O)[S:10][CH:11]=1)(=[O:4])=[O:3]>[Pd].O1CCCC1>[NH2:12][C:9]1[S:10][CH:11]=[C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:8]=1[S:15]([NH2:18])(=[O:16])=[O:17]

Participants

4

Reactant 1

HCID 59168801HCID 59168801, compound

Product 1

HCID 25065409HCID 25065409, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (10%, 0.150 g, dry) was added to a solution of 4-(methanesulfonylamino-methyl)-2-nitro-thiophene-3-sulfonic acid amide (0.156 g, 0.495 mmol) in tetrahydrofuran (12 mL) at 25° C. The flask was degassed and backfilled with hydrogen gas via balloon and the mixture was stirred under a positive pressure of hydrogen (2 balloons) for 17 h. The mixture was then filtered through Celite and the Celite was washed with tetrahydrofuran (3×20 mL). The combined filtrate and washings were concentrated in vacuo to afford the crude product, 2-amino-4-(methanesulfonylamino-methyl)-thiophene-3-sulfonic acid amide, as a yellow oil. This material was used in subsequent synthetic transformations without additional purification.

Workup

  1. customThe flask was degassed
  2. filtrationThe mixture was then filtered through Celite
  3. washthe Celite was washed with tetrahydrofuran (3×20 mL)
  4. concentrationThe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-eb72a8f16a9e40d6b43a4a92a55a42d5
Source dataset
uspto-grants-2012_07
Patent number
US08222404B2

Reaction notes

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