无水磷酸二氢钾 → 3-{Ethyl-[4-(5-nitro-benzo[c]isothiazol-3-ylazo)-phenyl]-amino}-propionic acid vinyl ester

HRID 252890

反应方程式

HRID 252890 反应方程式
N[C:2]1[C:10]2S[N:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.S(=O)(=O)(O)O.P(=O)(O)(O)O.[N:24](OS(=O)(=O)O)=O.[CH:31]([O:33][C:34](=[O:46])[CH2:35][CH2:36][N:37]([CH2:44][CH3:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[CH2:32].[S:47](=O)(=O)(O)[NH2:48]>CO>[CH:31]([O:33][C:34](=[O:46])[CH2:35][CH2:36][N:37]([CH2:44][CH3:45])[C:38]1[CH:43]=[CH:42][C:41]([N:24]=[N:8][C:7]2[S:47][N:48]=[C:10]3[CH:2]=[CH:3][C:4]([N+:11]([O-:13])=[O:12])=[CH:5][C:6]=23)=[CH:40][CH:39]=1)=[CH2:32]

参与物

8

反应物 6

HCID 1004无水磷酸二氢钾HCID 1118四氧化硫HCID 5987氨基磺酸HCID 82157亚硝基硫酸HCID 200389757-Amino-5-nitrobenzisothiazoleHCID 672669143-(Ethyl-phenyl-amino)-propionic acid vinyl ester

产物 1

HCID 591415113-{Ethyl-[4-(5-nitro-benzo[c]isothiazol-3-ylazo)-phenyl]-amino}-propionic acid vinyl ester

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

反应条件

温度
60 °C

实验过程

5.9 parts of 7-amino-5-nitrobenzisothiazole, 30 parts of 98% sulfuric acid and 8 parts of 85% phosphoric acid were charged, heated at 60° C. for 30 mins, then cooled to 5° C. 11.4 parts of 40% (w/w) nitrosyl sulfuric acid were added, whilst the temperature was held below 10° C. The diazotization mixture was stirred for a further 2 hrs at 5-10° C. To a separate vessel were charged 6.5 parts of 3-(ethyl-phenyl-amino)-propionic acid vinyl ester, 100 parts of methanol, 1 part sulfamic acid and 100 parts of ice. With stirring, the diazotization mixture was slowly added followed by a further 300 parts of ice. The reaction mixture was stirred over night and the product was isolated by filtration, washed with water and dried to yield 10.1 parts of 3-{ethyl-[4-(5-nitro-benzo[c]isothiazol-3-ylazo)-phenyl]-amino}-propionic acid vinyl ester. λmax=606 nm (DMF).

后处理

  1. temperaturecooled to 5° C
  2. customwas held below 10° C
  3. stirringWith stirring
  4. additionthe diazotization mixture was slowly added
  5. stirringThe reaction mixture was stirred over night
  6. customthe product was isolated by filtration
  7. washwashed with water
  8. customdried

来源与证据

ORD记录
ord-a91548c9c95d4b949953dc810420b30e
来源数据集
uspto-grants-2011_01
专利号
US07871446B2

关联笔记

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