Triethylamine → [(E)-(6-methoxy-2,3-dihydroinden-1-ylidene)amino] methanesulfonate

HRID 577471Notes

Reaction equation

HRID 577471 reaction equation
[OH:1]/[N:2]=[C:3]1\[CH2:4][CH2:5][C:6]2[C:11]\1=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4]/[C:3]/2=[N:2]\[O:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11389720Oxime-2,3-dihydro-6-methoxy-1H-inden-1-one

Product 1

HCID 89350921[(E)-(6-methoxy-2,3-dihydroinden-1-ylidene)amino] methanesulfonateYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1E)-N-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-imine (1a, 28.0 g, 158 mmol), DMAP (1.93 g, 15.8 mmol) and Et3N (63.8 g, 632 mmol) in dry DCM (200 mL) was added MsCl (27.5 g, 239 mmol) dropwise at 0° C. After the addition, the resulting solution was stirred at room temperature for 14 hours. The reaction mixture was washed with water (150 mL), saturated NH4Cl (130 mL) and brine (130 mL). The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 1:1) to give (1E)-6-methoxy-N-[(methylsulfonyl)oxy]-2,3-dihydro-1H-inden-1-imine (1b, 27 g, 67%) as a yellow solid.

Workup

  1. additionAfter the addition
  2. washThe reaction mixture was washed with water (150 mL), saturated NH4Cl (130 mL) and brine (130 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (petroleum ether/EtOAc, 1:1)

Sources & evidence

ORD record
ord-3db53b1a8b7f4c048c51a3a1cde3d096
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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