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

HRID 1018479노트

반응식

HRID 1018479 반응식
Cl.[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:16][NH:15][CH:14]([CH2:17][OH:18])[CH:13]=[C:12]2[CH3:19])=[CH:7][CH:6]=1)[CH3:3].C(N(CC)CC)C.[C:27]([NH:30][C:31]1[CH:40]=[CH:39][C:34]([S:35](Cl)(=[O:37])=[O:36])=[CH:33][CH:32]=1)(=[O:29])[CH3:28]>ClCCl>[C:27]([NH:30][C:31]1[CH:32]=[CH:33][C:34]([S:35]([N:15]2[CH:14]([CH2:17][OH:18])[CH:13]=[C:12]([CH3:19])[CH:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:2][CH3:3])=[CH:10][CH:9]=3)[O:16]2)(=[O:37])=[O:36])=[CH:39][CH:40]=1)(=[O:29])[CH3:28]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 184015523,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine hydrochloride

생성물 1

HCID 184015412-(4-acetamidobenzenesulphonyl)-3,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 3,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine hydrochloride (1.31 g, 4.59 mmol) and triethylamine (1.34 ml, 9.63 mmol) in dichloromethane (50 ml) was added 4-N-acetylsulphanilyl chloride (1.07 g, 4.59 mmol). After 4 h at room temperature, the reaction mixture was washed twice with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to a foam, purified on flash silica eluting with ethylacetate to give 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine as a white foam. 1H NMR (CDCl3)δ 1.39(3H, t), 2.21(3H, s), 3.85(2H, m), 4.00(2H, q), 4.54(1H, m), 5.32(1H, s), 5.70(1H, m), 6.80(2H, d), 7.09(2H, d), 7.54(1H, bs) 7.63(2H, d), 7.85(2H, d).

후처리

  1. washthe reaction mixture was washed twice with water and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to a foam
  5. custompurified on flash silica eluting with ethylacetate

출처 및 근거

ORD 기록
ord-33fc6026df534aa6b200b335beed61a6
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482824B1

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