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

HRID 2239250
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HRID 2239250 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-93d976cf4a10436c9c214245d6aa95a7
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723326B2

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