Chloroacetyl chloride → 2-chloro-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindolin-4-yl}acetamide

HRID 433282

반응식

HRID 433282 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[NH2:28])[C:19]2=[O:29])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[Cl:30][CH2:31][C:32](Cl)=[O:33]>CCOCC>[Cl:30][CH2:31][C:32]([NH:28][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:25]=1[C:26](=[O:27])[N:18]([CH:12]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:19]2=[O:29])=[O:33]

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 98449131H-Isoindole-1,3(2H)-dione, 4-amino-2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-

생성물 1

HCID 187583732-chloro-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindolin-4-yl}acetamide수율 96%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A mixture of 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-aminoisoindoline-1,3-dione (2.0 g, 4.8 mmol) and chloroacetyl chloride (2 mL, 25 mmol) was heated to reflux for 30 minutes. The solvent was removed in vacuo to give a solid. The solid was stirred in ether (40 mL) for 1 hour to give a suspension. The suspension was filtered and washed with ether to give 2-chloro-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindolin-4-yl}acetamide as a white solid (2.28 g, 96% yield); mp, 166-168° C.; 1H NMR (CDCl3) δ1.48 (t, J=6.9 Hz, 3H, CH3), 2.88 (s, 3H, CH3), 3.75 (dd, J=4.4, 14.3 Hz, 1H, CHH), 3.86 (s, 3H, CH3), 4.13 (q, J=7.0 Hz, 2H, CH2), 4.24 (s, 2H, CH2), 4.57 (dd, J=10.5, 14.3 Hz, 1H, CHH), 5.89 (dd, J=4.5, 10.3 Hz, 1H, NCH), 6.84-6.88 (m, 1H, Ar), 7.11-7.15 (m, 2H, Ar), 7.57 (d, J=7.2 Hz, 1H, Ar), 7.70 (t, J=7.6 Hz, 1H, Ar), 8.77 (d, J=8.3 Hz, 1H, Ar), 10.53 (s, 1H, NH); 13C NMR (CDCl3) δ14.60, 41.52, 42.67, 48.72, 54.51, 55.88, 64.48, 111.46, 112.44, 116.37, 119.06, 120.38, 124.74, 129.17, 131.22, 136.04, 136.29, 148.58, 149.75, 165.21, 167.25, 169.01; Anal Calcd for C22H23N2O7ClS+0.1 H2O: C, 53.19; H, 4.71; N, 5.50; H2O, 0.36. Found: C, 52.89; H, 4.52; N, 5.50; H2O, 0.17.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customThe solvent was removed in vacuo
  4. customto give a solid
  5. customto give a suspension
  6. filtrationThe suspension was filtered
  7. washwashed with ether

출처 및 근거

ORD 기록
ord-25187df30e584b1bae357c909ba009f4
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667316B1

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