Acetic Acid → HCID 178427610, compound

HRID 1502632Notes

Reaction equation

HRID 1502632 reaction equation
C([O:8][CH2:9][CH2:10][NH:11][C:12]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[NH:13])C1C=CC=CC=1.C.CCOC(C)=O.CCCCC.C(O)(=O)C>CO.[Pd]>[OH:8][CH2:9][CH2:10][NH:11][C:12]([NH:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)(=[O:17])=[O:16])=[NH:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297Methane2×HCID 22335286Ethyl acetate pentaneHCID 178427611HCID 178427611, compound

Product 1

HCID 178427610HCID 178427610, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

83.8 mg (0.24 mmol) of N—(N-(2-(benzyloxy)ethyl)carbamimidoyl)-4-methylbenzenesulfonamide were dissolved under nitrogen in MeOH. A few mg of 10% Palladium over activated charcoal were added. 3 vacuo hydrogen flush were done before stirring vigorously the reaction under a H2 atmosphere. After 2 hours, no conversion was found by TLC (eluant AcOEt:pentane 9:1) and approximatively 5 times the amount of starting Palladium over activated charcoal was added. The rection was stirred overnight. The TLC showed the formation of a more polar product unless the reaction was far from being complete. 1 mL of acetic acid was added. One hour after the reaction was complete. The reaction was filtered over celite and the solvent evaporated to afford 62.8 mg (0.24 mmol) of N—(N-(2-hydroxyethyl)carbamimidoyl)-4-methylbenzenesulfonamide as a white solid (yield=100%).

Workup

  1. custom3 vacuo hydrogen flush
  2. customthe reaction under a H2 atmosphere
  3. additionwas added
  4. stirringThe rection was stirred overnight
  5. customOne hour
  6. filtrationThe reaction was filtered over celite
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-59a38e2bef664b5aa60fe247c42dbb80
Source dataset
uspto-grants-2015_12
Patent number
US09211340B2

Reaction notes

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