Propionic Acid → HCID 86611143, compound

HRID 900383Notes

Reaction equation

HRID 900383 reaction equation
NC1S[C:4]([N+:7]([O-])=O)=[CH:5]N=1.C(O)(=[O:13])CC.N(OS(=O)(=O)O)=O.S(=O)(=O)(O)N.[N+:27]([C:30]1[S:34][C:33]([N:35]=[N:36][C:37]2[CH:55]=[CH:54][C:40]([N:41]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:42][CH2:43][C:44](OCC#N)=[O:45])=[CH:39][CH:38]=2)=[N:32][CH:31]=1)([O-:29])=[O:28]>CC(C)=O.O.C(O)(=O)C>[N+:27]([C:30]1[S:34][C:33]([N:35]=[N:36][C:37]2[CH:38]=[CH:39][C:40]([N:41]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:42][C:43](=[C:44]=[O:45])[O:13][CH2:5][C:4]#[N:7])=[CH:54][CH:55]=2)=[N:32][CH:31]=1)([O-:29])=[O:28]

Participants

9

Reactant 5

HCID 1032Propionic AcidHCID 5987Sulfamic AcidHCID 84862-Amino-5-NitrothiazoleHCID 82157Nitrosylsulfuric acidHCID 58827601HCID 58827601, compound

Product 1

HCID 86611143HCID 86611143, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

2-amino-5-nitrothiazole (2.9 parts) was set stirring at 5° C. with a mixture of acetic acid and propionic acid, 86:14 (50 parts). Nitrosyl sulphuric acid 40% (7.0 parts) was added below 5° C. and the mixture was stirred for 30 mins. The diazo solution was added gradually to a stirred coupling mixture of N-butyl, N-2(cyanomethoxycarbonylethyl)-aniline (5.2 parts), acetone (50 parts), water (200 parts) and sulphamic acid (0.5 parts). After one hour the product was isolated by filtration, washed with cold water and dried to yield, 4-(5-nitrothiazol-yl-azo)-N-butyl-N-(2-cyanomethoxycarbonylethyl)aniline (2.9 parts) λmax=571 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-3eb5f1935e9947718cac28cc80f74c34
Source dataset
uspto-grants-2008_04
Patent number
US07358345B2

Reaction notes

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