Hydrochloric Acid → HCID 135593875、化合物

HRID 2287008ノート

反応式

HRID 2287008 の反応式
[NH2:1]C1C2C(=CC=CC=2)C(O)=C(C(NCCCCOC2C=CC(C(CC)(C)C)=CC=2C(CC)(C)C)=O)C=1.[C:37]([NH:40][C:41]1[C:50]2[C:45](=[C:46]([N:52]=[N:53][C:54]3[CH:59]=[CH:58][C:57]([S:60]([Cl:63])(=[O:62])=[O:61])=[CH:56][CH:55]=3)[CH:47]=[CH:48][C:49]=2[OH:51])[C:44]([S:64]([Cl:67])(=[O:66])=[O:65])=[CH:43][CH:42]=1)(=[O:39])[CH3:38].Cl.[C:69]([NH:72][C:73]1[C:82]2[C:77](=[CH:78][CH:79]=[C:80](N=NC3C=CC(S(=O)(=O)N)=CC=3)[C:81]=2[OH:83])[C:76]([S:96]([O-:99])(=[O:98])=[O:97])=[CH:75][CH:74]=1)(=[O:71])[CH3:70].[Na+:100].ClS(O)(=O)=O>N1C=CC=CC=1>[C:37]([NH:40][C:41]1[C:50]2[C:45](=[C:46]([N:52]=[N:53][C:54]3[CH:55]=[CH:56][C:57]([S:60]([Cl:63])(=[O:61])=[O:62])=[CH:58][CH:59]=3)[CH:47]=[CH:48][C:49]=2[OH:51])[C:44]([S:64]([Cl:67])(=[O:65])=[O:66])=[CH:43][CH:42]=1)(=[O:39])[CH3:38].[C:69]([NH:72][C:73]1[C:82]2[C:77](=[C:78]([N:52]=[N:53][C:54]3[CH:59]=[CH:58][C:57]([S:60](=[O:62])(=[O:61])[NH2:1])=[CH:56][CH:55]=3)[CH:79]=[CH:80][C:81]=2[OH:83])[C:76]([S:96]([O-:99])(=[O:97])=[O:98])=[CH:75][CH:74]=1)(=[O:71])[CH3:70].[Na+:100]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 30848622-Naphthalenecarboxamide, 4-amino-N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-HCID 135593873HCID 135593873、化合物HCID 135593879HCID 135593879、化合物

生成物 2

HCID 135593875HCID 135593875、化合物HCID 135593879HCID 135593879、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1.95 g. (0.004 mol) of 4-amino-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-1-hydroxy-2-naphthamide in 50 ml. of dry pyridine at 0° C., under nitrogen, was added 1.95 g. (0.004 mol) of 4-acetamido-8-(4-chlorosulfonylphenylazo)-5-hydroxy-1-naphthalenesulfonyl chloride. The solution was stirred at 0° C. for one hour, poured into 75 ml. of concentrated hydrochloric acid and 75 ml. of ice. The solid was collected on a filter funnel and dried. It was then chromatographed on a silica column, eluting with ethyl acetate to remove the product. The eluents were concentrated to dryness and the resulting solid reprecipitated from chloroform with hexane. The solid was collected on a filter funnel and dried to yield 1.1 g. (39%), m.p. 220°-2° C. dec. The 4-acetamido-8-(4-chlorosulfonylphenylazo)-5-hydroxy-1-naphthalenesulfonyl chloride was prepared by heating a solution of 9.7 g. (0.02 mol) of sodium 4-acetamido-5 -hydroxy-6-(4-sulfamoylphenylazo)-1-naphthalenesulfonate in 150 ml. of chlorosulfonic acid on a steam bath for ninety minutes. The solution was cooled and poured onto ice. The solid was collected on a filter funnel and dried to yield 9.4 g. (94%). The sodium 4-acetamido-5-hydroxy-8-(4-sulfamoylphenylazo)-1-naphthalenesulfonate was prepared as in Example 1.

後処理

  1. additionpoured into 75 ml
  2. customThe solid was collected on a filter funnel
  3. customdried
  4. customIt was then chromatographed on a silica column
  5. washeluting with ethyl acetate
  6. customto remove the product
  7. concentrationThe eluents were concentrated to dryness
  8. customthe resulting solid reprecipitated from chloroform with hexane
  9. customThe solid was collected on a filter funnel
  10. customdried
  11. customto yield 1.1 g
  12. temperatureby heating a solution of 9.7 g
  13. temperatureThe solution was cooled
  14. additionpoured onto ice
  15. customThe solid was collected on a filter funnel
  16. customdried
  17. customto yield 9.4 g

出典と根拠

ORDレコード
ord-6dccf83a06824255a52e6905e97105cc
出典データセット
uspto-grants-1981_05
特許番号
US04268606

反応ノート

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