Water → 5-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 565202Notes

Reaction equation

HRID 565202 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][OH:10].C(N(CC)CC)C.[C:18](Cl)(Cl)=[O:19].O>C1COCC1.CCOC(C)=O>[CH3:8][C:4]1[C:3]2[CH2:9][O:10][C:18](=[O:19])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 8471TriethylamineHCID 15339417(2-Amino-6-methylphenyl)methanol

Product 1

HCID 105589525-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-amino-6-methyl-phenyl)-methanol (2.74 g, 20 mmol) and triethylamine (4.04 g, 40 mmol) in THF (150 mL), phosgene (12.5% solution in toluene, 17.42 g, 22 mrnol) was added dropwise at 0° C. Reaction mixture was allowed to warm to room temperature and stirred for 16 hours. Water (150 mL) was added under stirring, followed by EtOAc (2×100 mL). EtOAc extracts were washed with water and brine and dried over MgSO4. The product (buff solid) was crystallized from EtOAc:pet. ether mixture. (Yield: 2.37=73%); mp 222-226° C.; MS (CI): M+1=163.

Workup

  1. customReaction mixture
  2. stirringunder stirring
  3. washEtOAc extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe product (buff solid) was crystallized from EtOAc

Sources & evidence

ORD record
ord-b3e1020e7dd043be888f31f3f0ddc99e
Source dataset
uspto-grants-2001_01
Patent number
US06172065B2

Reaction notes

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