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

HRID 252890

반응식

HRID 252890 반응식
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]

참가 물질

8

반응물 6

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 5987Sulfamic AcidHCID 82157Nitrosylsulfuric acidHCID 200389757-Amino-5-nitrobenzisothiazoleHCID 672669143-(Ethyl-phenyl-amino)-propionic acid vinyl ester

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a91548c9c95d4b949953dc810420b30e
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07871446B2

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