Methyl morpholine oxide → n-Cyclobutyl-5-(2,6-dichloro-4-formyl-phenoxy)-2-hydroxy-n-methyl-benzamide

HRID 1168097Notes

Reaction equation

HRID 1168097 reaction equation
Br[CH2:2][C:3]1[CH:24]=[C:23]([Cl:25])[C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([OH:22])=[C:12]([CH:21]=2)[C:13]([N:15]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[CH3:16])=[O:14])=[C:5]([Cl:26])[CH:4]=1.C[N+]1([O-])CC[O:31]CC1>C(#N)C>[CH:17]1([N:15]([CH3:16])[C:13](=[O:14])[C:12]2[CH:21]=[C:8]([O:7][C:6]3[C:23]([Cl:25])=[CH:24][C:3]([CH:2]=[O:31])=[CH:4][C:5]=3[Cl:26])[CH:9]=[CH:10][C:11]=2[OH:22])[CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22285658HCID 22285658, compound

Product 1

HCID 22285661n-Cyclobutyl-5-(2,6-dichloro-4-formyl-phenoxy)-2-hydroxy-n-methyl-benzamideYield 79.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the title compound of Step G (130 mg, 0.28 mmol) in dry acetonitrile (6 ml) at room temperature under nitrogen was added molecular seives (4 A°, 50 mg). After stirring for about 15 minutes at room temperature, N-methylmorpholine N-oxide (66 mg, 0.57 mmol) was added. The resulting mixture was stirred at room temperature for about 18 hours, then filtered through a short pad of silica gel with an acetonitrile wash. The filtrate was concentrated to afford the title compound (88 mg) as an off-white foam which was used in the next step without further purification. MS (APCl−) Calc: 393.1, found: 392.1 (M−1).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for about 18 hours
  2. filtrationfiltered through a short pad of silica gel with an acetonitrile
  3. washwash
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-879e22ff18914c70ae6891b21912eb3f
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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