Nitric Acid → HCID 19100755, compound

HRID 1974966Notes

Reaction equation

HRID 1974966 reaction equation
[C:1]([NH:8][C:9]1[S:10][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[N+:17]([O-])([OH:19])=[O:18]>C(OC(=O)C)(=O)C.C(O)(=O)C>[C:1]([NH:8][C:9]1[S:10][C:11]([CH:14]([CH3:15])[CH3:16])=[CH:12][C:13]=1[N+:17]([O-:19])=[O:18])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 19100732Ethyl 2-[[5-(1-methylethyl)-2-thienyl]amino]-2-oxoacetate

Product 1

HCID 19100755HCID 19100755, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-10 °C

Procedure

2-Ethoxalylamino-5-isopropylthiophene (6.9 g, 28.5 mol) was dissolved in 50 ml of acetic anhydride, cooled to -10° C., and treated with a solution of fuming nitric acid (1.8 g, 28.5 mmol) in 15 ml of acetic acid. After 20 minutes, the mixture was evaporated in vacuo to yield 8.4 g of crude product which was purified by chromatography on silica gel (toluene:acetone 95:5), to yield 4.8 g (57%) of 2-ethoxalylamino-5-isopropyl-3-nitrothiophene. 1H-NMR (CDCl3, δ): 1.3 (d, 6H), 1.5 (t, 3H), 3.1 (m, 1H), 4.5 (q, 2H), 12.0 (s, 1H).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customto yield 8.4 g of crude product which
  3. customwas purified by chromatography on silica gel (toluene:acetone 95:5)

Sources & evidence

ORD record
ord-a579f97b5df0490ea293eeb0f37658e3
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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