Acetic Acid → HCID 178427494, compound

HRID 1502634Notes

Reaction equation

HRID 1502634 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[NH:17])C1C=CC=CC=1.C.C(O)(=O)C>CO.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=1)(=[O:21])=[O:20])=[NH:17]

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 297Methane2×HCID 178427495HCID 178427495, compound

Product 1

HCID 178427494HCID 178427494, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

3.20 g (7.9 mmol) of N—(N-(6-(benzyloxy)hexyl)carbamimidoyl)-4-methylbenzenesulfonamide were dissolved under nitrogen in MeOH. A few mg of 10% Palladium over activated charcoal were added. 1 mL of acetic acid was added. 3 vacuo hydrogen flush were done before stirring vigorously the reaction under a H2 atmosphere. The reaction was vigorously stirred at room temperature for 3 hours and checked by TLC. No conversion was found and 2 mL of acetic acid were added. After 1 hour, the TLC showed no conversion and more 10% Palladium over activated charcoal were added. After 3 days, the TLC showed a complete conversion and the solution was filtered over celite and the solvent evaporated to afford 2.480 g of N—(N-(6-hydroxyhexyl)carbamimidoyl)-4-methylbenzenesulfonamide as slightly yellow oil was obtained (yield=100%).

Workup

  1. custom3 vacuo hydrogen flush
  2. customthe reaction under a H2 atmosphere
  3. stirringThe reaction was vigorously stirred at room temperature for 3 hours
  4. additionwere added
  5. waitAfter 3 days
  6. filtrationthe solution was filtered over celite
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-a364f1c205684fb89faf1cc9a6ef6a08
Source dataset
uspto-grants-2015_12
Patent number
US09211340B2

Reaction notes

Loading…