m-Tolyl isocyanate → 6-Methyl-6-phenyl-3-m-tolyl-1,3-oxazinan-2-one

HRID 2037391Notes

Reaction equation

HRID 2037391 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]([OH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1.[CH3:34][C:35]1[CH:36]=[C:37]([N:41]=[C:42]=[O:43])[CH:38]=[CH:39][CH:40]=1>C(Cl)Cl>[CH3:15][C:14]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:22][C:42](=[O:43])[N:41]([C:37]2[CH:36]=[C:35]([CH3:34])[CH:40]=[CH:39][CH:38]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 534742853-Hydroxy-3-phenylbutyl 4-methylbenzenesulfonate

Product 1

HCID 251833146-Methyl-6-phenyl-3-m-tolyl-1,3-oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (1 g, 3.12 mmol) and DBU (1.4 g, 9.26 mmol) in CH2Cl2 (15 mL) was added a solution of 3-methylphenyl isocyanate (623 mg, 4.68 mmol) in CH2Cl2 (5 mL) at 0° C. over 0.5 h. The mixture was stirred at rt overnight. The mixture was concentrated to give the crude product, which was purified by column chromatography and then by preparative HPLC to afford 6-methyl-6-phenyl-3-m-tolyl-1,3-oxazinan-2-one. LC-MS Method 2, tR=2.706 min, m/z=282. 1H NMR (CDCl3) 1.75 (s, 3H), 2.30 (s, 3H), 2.35-2.50 (m, 2H), 3.30 (m, 1H), 3.50 (m, 1H), 6.95 (m, 2H), 7.05 (m, 1H), 7.20-7.30 (m, 1H), 7.35 (m, 1H), 7.42-7.50 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a5c98d04a04548628f373ffdc8707a8f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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