Acetic Acid → HCID 58598892, compound

HRID 1020336Notes

Reaction equation

HRID 1020336 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.C(O)(=O)C.C(=O)(OCC)N.[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:25](=[O:33])[CH:26]3[CH2:32][NH:31][CH2:30][CH:27]3[C:28]=2[CH:29]=1>ClCCCl>[Cl:8][C:29]1[C:28]2[CH:27]3[CH2:30][NH:31][CH2:32][CH:26]3[C:25](=[O:33])[C:24]=2[CH:23]=[CH:22][C:21]=1[O:20][CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 67204358HCID 67204358, compound

Product 1

HCID 58598892HCID 58598892, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

NCS (0.25 g, 1.9 mmol) and acetic acid (10 mL) were added to a solution of ethyl carbamate-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one (0.52 g, 1.9 mmol) in DCE (10 mL), and stirred overnight at 60° C. The reaction was quenched with aqueous HCl (1 M) and washed with brine. The organic extracts were dried over MgSO4, and concentrated. The crude product was purified by column chromatography (SiO2) using a 0-60% EtOAc-hexanes gradient to afford the subtitle compound as a mixture of regioisomers. MS calculated for C15H16ClNO4+H: 310, observed: 310.

Workup

  1. customThe reaction was quenched with aqueous HCl (1 M)
  2. washwashed with brine
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-9df47356920348e7a544bd3dd4e5b65a
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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