Hydrochloric Acid → HCID 135593875, compound

HRID 2287008Notes

Reaction equation

HRID 2287008 reaction equation
[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]

Participants

8

Reactant 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, compoundHCID 135593879HCID 135593879, compound

Product 2

HCID 135593875HCID 135593875, compoundHCID 135593879HCID 135593879, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6dccf83a06824255a52e6905e97105cc
Source dataset
uspto-grants-1981_05
Patent number
US04268606

Reaction notes

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