Urea → 4-(2-nitro-4-heptadecyloxycarbonylphenylazo)-N-methyl-N-(2-[hydroxycarbonyl]ethyl)aniline

HRID 728407Notes

Reaction equation

HRID 728407 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].N(OS(=O)(=O)O)=O.[NH2:38]C(N)=O.[CH3:42][N:43]([CH2:50][CH2:51][C:52]([OH:54])=[O:53])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C([O-])(=O)C.[Na+]>O>[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:12])[CH:8]=[CH:7][C:5]=1[N:6]=[N:38][C:47]1[CH:48]=[CH:49][C:44]([N:43]([CH3:42])[CH2:50][CH2:51][C:52]([OH:54])=[O:53])=[CH:45][CH:46]=1)([O-:3])=[O:2]

Participants

8

Reactant 6

HCID 1176UreaHCID 82157Nitrosylsulfuric acidHCID 517045Sodium AcetateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 125224893-(Methylphenylamino)-propionic acidHCID 198239524-Heptadecyloxycarbonyl-2-nitroaniline

Product 1

HCID 198239484-(2-nitro-4-heptadecyloxycarbonylphenylazo)-N-methyl-N-(2-[hydroxycarbonyl]ethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Nitro-4-(heptadecyloxycarbonyl)aniline (0.42 g) was added to cold nitrosyl-sulphuric acid (70 mg of sodium nitrite and 1.5 ml of 98% sulphuric acid) and stirred at 0°-5° C. for 1.5 hours. Urea (0.1 g) was added and then the resulting mixture was added to a cold solution of N-methyl-N-(2-hydroxycarbonylethyl)aniline in a 1:1 mixture of acetic and propionic acids (10 ml). Sodium acetate was added and the reaction mixture was stirred for 1 hour after which time it was diluted with water and filtered. The red solid was purified by chromatography to give red product (yield: 0.15 g; mass spec: M+, 610).

Workup

  1. stirringthe reaction mixture was stirred for 1 hour after which time it
  2. filtrationfiltered
  3. customThe red solid was purified by chromatography
  4. customto give red product (yield: 0.15 g; mass spec: M+, 610)

Sources & evidence

ORD record
ord-f1af6aa097254bc184f248ccaf03c89e
Source dataset
uspto-grants-1991_09
Patent number
US05047516

Reaction notes

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