Propionic Acid → HCID 86611142, compound

HRID 900382Notes

Reaction equation

HRID 900382 reaction equation
Cl[C:2]1C=C([N+]([O-])=O)C=C(Cl)[C:3]=1[NH2:4].C(O)(=[O:16])CC.N(OS(=O)(=O)O)=O.S(=O)(=O)(O)N.[Cl:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([Cl:40])[C:32]=1[N:41]=[N:42][C:43]1[CH:59]=[CH:58][C:46]([N:47]([CH2:56][CH3:57])[CH2:48][CH2:49][C:50](OCC#N)=[O:51])=[CH:45][CH:44]=1>CC(C)=O.O.CO.C(O)(=O)C>[Cl:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([Cl:40])[C:32]=1[N:41]=[N:42][C:43]1[CH:44]=[CH:45][C:46]([N:47]([CH2:56][CH3:57])[CH2:48][C:49](=[C:50]=[O:51])[O:16][CH2:2][C:3]#[N:4])=[CH:58][CH:59]=1

Participants

10

Reactant 5

HCID 1032Propionic AcidHCID 5987Sulfamic AcidHCID 74302,6-Dichloro-4-nitroanilineHCID 82157Nitrosylsulfuric acidHCID 58827605HCID 58827605, compound

Product 1

HCID 86611142HCID 86611142, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2,6-dichloro-4-nitroaniline (6.2 parts) was set stirring at 5° C. with a mixture of acetic acid and propionic acid, 86:14 (40 parts). Nitrosyl sulphuric acid 40% (11.4 parts) was added below 5° C. and the mixture was stirred for 30 minutes. The diazo solution was added gradually to a stirred coupling mixture of N-ethyl, N-2(cyanomethoxycarbonylethyl)-aniline (8.3 parts), methanol (50 parts), water (300 parts) and sulphamic acid (1 part). After one hour the product was isolated by filtration, washed with cold water and dried to yield, 4-(2,6-dichloro-4-nitrophenylazo)-N-ethyl-N-(2-cyanomethoxycarbonylethyl)aniline (9.5 parts) λmax=432 nm (acetone).

Workup

  1. customAfter one hour the product was isolated by filtration
  2. washwashed with cold water
  3. customdried
  4. customto yield

Sources & evidence

ORD record
ord-d846e7ce52614d368634f515c7fbeaa3
Source dataset
uspto-grants-2008_04
Patent number
US07358345B2

Reaction notes

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