Triethylamine → 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

HRID 1018473노트

반응식

HRID 1018473 반응식
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl.[CH3:23][CH:24]1[CH:29]=[C:28]([CH3:30])[CH:27]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[CH:33][CH:32]=2)[O:26][NH:25]1>ClCCl>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([N:25]2[CH:24]([CH3:23])[CH:29]=[C:28]([CH3:30])[CH:27]([C:31]3[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH3:39])=[CH:35][CH:36]=3)[O:26]2)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 184015323,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride

생성물 1

HCID 98455822-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred suspension of 4-N-acetylsulphanilyl chloride (1.14 g, 4.9 mmol) and triethylamine (0.82 g, 8.15 mmol) in dichloromethane (15 ml) was added a solution of 3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride (0.88 g, 3.26 mmol) in dichloromethane (15 ml). The resulting solution was stirred at room temperature for 8 h then washed with water three times, aqueous sodium hydroxide (2M), water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to a foam. The crude product was purified on flash silica eluting with ethylacetate-hexane (3:2) to give 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine as a white foam. 1H NMR (CDCl3) δ 1.41(9H, m), 2.14(3H, s), 4.01(2H, q), 4.43(1H, m), 5.17(1H, s), 5.66(1H, d), 6.79(2H, d), 7.11(2H, d), 7.60(2H, d), 7.79(2H, d), 7.89(1H, bs).

후처리

  1. washthen washed with water three times, aqueous sodium hydroxide (2M), water and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to a foam
  5. customThe crude product was purified on flash silica eluting with ethylacetate-hexane (3:2)

출처 및 근거

ORD 기록
ord-26c068e13d2a4eb794407c4b503c756e
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482824B1

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