海萝胶 → Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

HRID 14000

反应方程式

HRID 14000 反应方程式
N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[ClH:21].N([O-])=O.[Na+].[S:26](=[O:28])=[O:27]>C(O)(=O)C.O>[Cl:21][S:26]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:28])=[O:27]

参与物

7

反应物 4

HCID 313海萝胶HCID 1119二氧化硫HCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]BenzoateHCID 23668193亚硝酸钠

产物 1

HCID 22593631Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

试剂、催化剂与溶剂 2

HCID 176醋酸溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

Methyl 3-amino-5-[(dipropylamino)carbonyl]benzoate (XXXI, PREPARATION 10, 1.11 g, 4 mmol) is added to a mixture of water (5 mL) and concentrated hydrochloric acid (1 mL). Sodium nitrite (0.276 g, 4 mmol) is added to the mixture slowly at 0 degrees C. The mixture is then added to an acetic acid solution (5 mL) of CuCl2.2H2O saturated with sulfur dioxide. The mixture is stirred for 0.5 hours and poured into ice water. The mixture is extracted with ethyl acetate. The organic phase is separated and washed with saturated sodium bicarbonate, water, and saline and dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 8.69, 8.38, 8.20, 4.01, 3.49, 3.14, 1.72, 159, 1.01 and 0.79; MS (ESI+) for C15H20ClNO5S m/z (M+H)+=362.2

后处理

  1. extractionThe mixture is extracted with ethyl acetate
  2. customThe organic phase is separated
  3. washwashed with saturated sodium bicarbonate, water, and saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

来源与证据

ORD记录
ord-8acc97aef642495381b2df7e9ffa2515
来源数据集
uspto-grants-2010_06
专利号
US07727997B2

关联笔记

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