2-(Dimethylamino)acetyl chloride hydrochloride → N-{3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}-2-dimethylaminoacetamide

HRID 2121962노트

반응식

HRID 2121962 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12](=[O:21])[C:11](=[C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[S:23]3)[S:10]2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:33][N:34]([CH2:36][C:37](Cl)=[O:38])[CH3:35]>C(Cl)(Cl)Cl>[CH2:14]([N:13]1[C:12](=[O:21])[C:11](=[C:22]2[N:26]([CH3:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[S:23]2)[S:10][C:9]1=[N:8][C:4]1[CH:3]=[C:2]([NH:1][C:37](=[O:38])[CH2:36][N:34]([CH3:35])[CH3:33])[CH:7]=[CH:6][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 72639856HCID 72639856, 화합물

생성물 1

HCID 72639860N-{3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}-2-dimethylaminoacetamide수율 18%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 2-(3-aminophenylimino)-3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)thiazolidine-4-one (160 mg, 360 μmol) in chloroform (8 mL) was added N,N-dimethylaminoacetyl chloride hydrochloride (90 mg, 0.58 mmol) and TEA (150 μL, 1.1 mmol). The reaction solution was heated at reflux for 20 h, cooled, and concentrated in vacuo. The crude material was chromatographed (silica gel, 0-50% EtOAc/Hex) to give the title compound (34 mg, 18%) as a yellow solid. 1H-NMR (CDCl3): δ 9.03 (1H, s), 7.50 (2H, d), 7.37 (2H, t), 7.17-7.26 (5H, m), 7.11 (1H, m), 7.05 (1H, t), 6.88 (1H, d), 6.68 (1H, d), 5.03 (2H), 3.60 (3H, s), 3.00 (2H, s), 2.28 (6H, s); MS(ESI): 530 (MH+).

후처리

  1. temperatureThe reaction solution was heated
  2. temperatureat reflux for 20 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed (silica gel, 0-50% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-a2fc8c6738d3446dbcf0c7215459cddd
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696473B2

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