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

HRID 703140Notes

Reaction equation

HRID 703140 reaction equation
[CH2:1]([O:18][C:19]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1)=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].N(OS(=O)(=O)O)=O.[NH2:38]C(N)=O.[C:42]([CH2:45][CH2:46][N:47]([CH3:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([OH:44])=[O:43].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C([O-])(=O)C.[Na+]>O>[N+:28]([C:23]1[CH:22]=[C:21]([C:19]([O:18][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:20])[CH:27]=[CH:26][C:24]=1[N:25]=[N:38][C:51]1[CH:52]=[CH:53][C:48]([N:47]([CH3:54])[CH2:46][CH2:45][C:42]([OH:44])=[O:43])=[CH:49][CH:50]=1)([O-:30])=[O:29]

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

4-Heptadecyloxycarbonyl-2-nitroaniline (0.42g) 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-(2-carboxyethyl)-N-methylaniline 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: 0.15g; 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: 0.15g; mass spec: M+, 610)

Sources & evidence

ORD record
ord-559dbdec424f4201aa2982c3105dd1a9
Source dataset
uspto-grants-1991_01
Patent number
US04981612

Reaction notes

Loading…