Nitric Acid → HCID 19100692, compound

HRID 1974968Notes

Reaction equation

HRID 1974968 reaction equation
[C:1]([NH:8][C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[N+:20]([O-])([OH:22])=[O:21]>C(OC(=O)C)(=O)C.C(O)(=O)C>[C:1]([NH:8][C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:13]=1[N+:20]([O-:22])=[O:21])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 19100803HCID 19100803, compound

Product 1

HCID 19100692HCID 19100692, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-15 °C

Procedure

2-Ethoxalylamino-5-phenylthiophene (2.75 g, 10 mmol) was dissolved in 20 ml of acetic anhydride, cooled to -15° C., and treated with a solution of 0.63 ml (10 mmol) of fuming nitric acid dissolved in 5 ml of acetic acid over a period of 30 minutes. After 10 minutes at this temperature, the solvents were evaporated, and traces of acetic acid were removed by stripping with toluene. The solid residue was suspended in 50 ml of ethanol, and 50 ml of water was slowly added. The mixture was stirred overnight, and the precipitate was isolated by filtration to yield 2.62 g (82%) of 2-ethoxalylamino-5-phenyl-3-nitrothiophene, melting at 139°-144° C. 1H-NMR (DMSO-D6, δ): 1.3 (t, 3H), 4.4 (q, 2H), 6.9 (t, 1H), 7.0 (t, 2H), 7.8 (d, 2H), 8.0 (s, 1H).

Workup

  1. customthe solvents were evaporated
  2. customtraces of acetic acid were removed
  3. addition50 ml of water was slowly added
  4. customthe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-dcd30e7159984ffb9fa9e9b317ce3f46
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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