HCID 135727397, compound → HCID 135727395, compound

HRID 972436Notes

Reaction equation

HRID 972436 reaction equation
[CH2:1]([N:13]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[S:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([OH:27])=[C:19]([N:28]=NC2C=CC(OC)=CC=2)[CH:18]=1)(=[O:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:50]([NH:53][C:54]1[C:63]2[C:58](=[CH:59][CH:60]=[C:61]([N:65]=[N:66][C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=3[O:73][CH3:74])[C:62]=2[OH:64])[C:57]([S:75](Cl)(=[O:77])=[O:76])=[CH:56][CH:55]=1)(=[O:52])[CH3:51]>O1CCCC1>[C:50]([NH:53][C:54]1[C:63]2[C:58](=[CH:59][CH:60]=[C:61]([N:65]=[N:66][C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=3[O:73][CH3:74])[C:62]=2[OH:64])[C:57]([S:75]([NH:28][C:19]2[CH:18]=[C:17]([S:14](=[O:16])(=[O:15])[N:13]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[OH:27])(=[O:77])=[O:76])=[CH:56][CH:55]=1)(=[O:52])[CH3:51]

Participants

4

Reactant 2

HCID 135727397HCID 135727397, compoundHCID 135755448HCID 135755448, compound

Product 1

HCID 135727395HCID 135727395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranCatalyst

Procedure

A solution of 3.47 g (0.0050 mole) 4-(N,N-didodecylsulfamyl)-2-(p-methoxyphenylazo)-1-naphthol in 50 ml tetrahydrofuran containing 0.5 g 5% palladium/carbon catalyst was hydrogenated at low pressure and room temperature for 2 hr. The mixture was filtered and poured into water, then extracted with ether. The extract was concentrated to a gum which was dissolved in 50 ml pyridine. The solution was cooled in an ice bath, and 2.17 g (0.005 mole) 4-acetamido-5-hydroxy-6-(o-methoxyphenylazo)naphthalene-1-sulfonyl chloride was added. The mixture was stirred overnight at room temperature, then poured into ice-water containing 50 ml concentrated hydrochloric acid. The purple solid was recrystallized from dichloroethane and ethyl acetate to give, after drying under vacuum, an amorphous solid (Compound No. 14), m.p. 200°-202° C.

Workup

  1. filtrationThe mixture was filtered
  2. additionpoured into water
  3. extractionextracted with ether
  4. concentrationThe extract was concentrated to a gum which
  5. dissolutionwas dissolved in 50 ml pyridine
  6. temperatureThe solution was cooled in an ice bath
  7. customThe purple solid was recrystallized from dichloroethane and ethyl acetate
  8. customto give
  9. customafter drying under vacuum

Sources & evidence

ORD record
ord-d42dbcc49ca24f05bf46f5d64fc73ed6
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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