Toluene → 4,4,6-Trimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 2239250Notes

Reaction equation

HRID 2239250 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].CCN(CC)CC.[C:20](Cl)(Cl)=[O:21].C1(C)C=CC=CC=1>C1COCC1>[CH3:11][C:9]1([CH3:10])[O:12][C:20](=[O:21])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 139590012-(2-Amino-5-methyl-phenyl)-propan-2-ol

Product 1

HCID 235552364,4,6-Trimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 14A (11.8 mmol, 1.95 g) in 200 mL THF was added Et3N (29.6 mmol, 4.06 mL) at 0° C. followed by a dropwise addition of a solution of phosgene in toluene (20% solution, 12.19 mmol, 7.9 mL). The reaction mixture was stirred at r.t. overnight It was extracted with Et2O, washed with water and brine. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuo to the desired product (2.14 g, expected wt.=2.25 g) which was used in the next step without further purification. MS (electrospray): mass calculated for C11H13NO2, 191.09, m/z found 192 (100%), [M+H]+.

Workup

  1. extractionwas extracted with Et2O
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo to the desired product (2.14 g
  6. customexpected wt.=2.25 g) which was used in the next step without further purification

Sources & evidence

ORD record
ord-93d976cf4a10436c9c214245d6aa95a7
Source dataset
uspto-grants-2010_05
Patent number
US07723326B2

Reaction notes

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