N-Hydroxyacetamidine → HCID 11823002, compound

HRID 1385294Notes

Reaction equation

HRID 1385294 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:15][C:6]2=[C:7]([C:12]([OH:14])=O)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:16])[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:30](=[N:33]O)([NH2:32])[CH3:31]>O1CCOCC1>[CH3:17][C:2]1([CH3:1])[CH2:15][C:6]2=[C:7]([C:12]3[O:14][N:33]=[C:30]([CH3:31])[N:32]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 30926N-HydroxyacetamidineHCID 682631,1'-CarbonyldiimidazoleHCID 2819767SBB053495

Product 1

HCID 11823002HCID 11823002, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one-1-carboxylic acid (1.0 g, 3.7 mmol) in dioxan (90 mL) was added carbonyldiimidazole (0.6 g, 3.7 mmol) and the mixture stirred at 20° C. for 30 min. Acetamide oxime (0.41 g, 5.5 mmol) was added and the mixture was heated at 100° C. for 48 h. The solution was evaporated to dryness and the residue was purified by chromatographed on silica gel, eluting with ethyl acetate:hexane (2:3) to yield the title compound as a pale yellow solid (0.1 g, 9%). mp 177-180° C. Found: C, 54.90; H, 5.05; N, 8.71%. C14H16N2O2S2 requires: C, 54.52; H, 5.23; N, 9.08%. 1HNMR (250 MHz, CDCl3) δ 1.11 (6H, s), 2.45-2.47 (5H, m), 2.65 (3H, s), 3.11 (2H, s). MS (ES+) 309 (M+1).

Workup

  1. temperaturethe mixture was heated at 100° C. for 48 h
  2. customThe solution was evaporated to dryness
  3. customthe residue was purified
  4. customby chromatographed on silica gel
  5. washeluting with ethyl acetate:hexane (2:3)

Sources & evidence

ORD record
ord-5f8de38ecde94354bc11869369d7e2f0
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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