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

HRID 2193442Notes

Reaction equation

HRID 2193442 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-a9ac1454a05446e680bcb0eb1d7a61d9
Source dataset
uspto-grants-2012_12
Patent number
US08329897B2

Reaction notes

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