Sulfuric Acid → HCID 178443736, compound

HRID 1748930Notes

Reaction equation

HRID 1748930 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]=[N:14][C:15]1[C:21]([O:22][CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][C:18]([NH2:19])=[C:17]([O:31][CH2:32][CH:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]=1)([O-:3])=[O:2].N(OS(=O)(=O)O)=O.S(=O)(=O)(O)O.[C:52]1([CH3:65])[CH:57]=[CH:56][CH:55]=[C:54]([N:58]([CH2:62][CH2:63][OH:64])[CH2:59][CH2:60][OH:61])[CH:53]=1.S(=O)(=O)(O)[NH2:67]>CN1C(=O)CCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1/[N:13]=[N:14]/[C:15]1[C:21]([O:22][CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][C:18](/[N:19]=[N:67]/[C:57]2[CH:56]=[CH:55][C:54]([N:58]([CH2:62][CH2:63][OH:64])[CH2:59][CH2:60][OH:61])=[CH:53][C:52]=2[CH3:65])=[C:17]([O:31][CH2:32][CH:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 5987Sulfamic AcidHCID 70732,2'-((3-Methylphenyl)imino)bisethanolHCID 82157Nitrosylsulfuric acidHCID 896020744-((2,4-Dinitrophenyl)diazenyl)-2,5-bis(2-ethylhexyloxy)aniline

Product 1

HCID 178443736HCID 178443736, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-((2,4-Dinitrophenyl)diazenyl)-2,5-bis(2-ethylhexyloxy)aniline (0.54 g, 1 mmol) is dissolved in NMP (10 ml) and to this is added 40% (w/w) nitrosyl sulfuric acid in sulfuric acid (0.38 g, 1.2 mmol). After 30 minutes, the mixture is added to a solution of 2,2′-(m-tolylazanediyl)diethanol (0.20 g, 1 mmol) and sulfamic acid (0.5 g) in IMS (100 ml). A dark oily solid separates immediately. After stirring overnight, the aqueous supernatant is decanted off, the oily solid washed with further water, then dried at 40° C. The pure title compound is acquired as a blue-black solid after multiple purifications over silica gel, eluting with dichloromethane containing an increasing concentration of ethyl acetate (0.54 g, 72%).

Workup

  1. customthe aqueous supernatant is decanted off
  2. washthe oily solid washed with further water
  3. customdried at 40° C
  4. washeluting with dichloromethane containing an increasing concentration of ethyl acetate (0.54 g, 72%)

Sources & evidence

ORD record
ord-44a018f633294a3597dde75543e99d4a
Source dataset
uspto-grants-2015_10
Patent number
US09152006B2

Reaction notes

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