Water → HCID 19100691, compound

HRID 1974969Notes

Reaction equation

HRID 1974969 reaction equation
[C:1]([NH:8][C:9]1[S:10][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:13]=1[N+:14]([O-])=O)([C:3](OCC)=[O:4])=[O:2].O>C(O)(=O)C.[Zn]>[C:17]1([C:11]2[S:10][C:9]3[NH:8][C:1](=[O:2])[C:3](=[O:4])[NH:14][C:13]=3[CH:12]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19100692HCID 19100692, compound

Product 1

HCID 19100691HCID 19100691, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-Ethoxalylamino-5-phenyl-3-nitrothiophene (641 mg, 2 mmol) was suspended in 35 ml of 80% acetic acid, and 1.31 g (20 mmol) of zinc dust was added in one portion with stirring. After 2 hours 70 ml of water was slowly added to the suspension, and the precipitate was isolated by filtration (483 mg). This crude product was purified by suspending in 20 ml of methylene chloride, filtering, and subsequent crystallisation by dissolving in 50 ml of boiling acetic acid and slow addition of 30 ml of water. The yield was 87 mg (17.8%) of the title compound as crystals, melting over 300° C. 1H-NMR (DMSO-D6, δ): 7.05 (s, 1H), 7.3 (t, 1H), 7.4 (t, 2H), 7.6 (d, 2H), 11.9-12.5 (broad, 2H).

Workup

  1. customthe precipitate was isolated by filtration (483 mg)
  2. customThis crude product was purified
  3. filtrationfiltering
  4. customsubsequent crystallisation
  5. dissolutionby dissolving in 50 ml of boiling acetic acid
  6. additionslow addition of 30 ml of water
  7. custommelting over 300° C

Sources & evidence

ORD record
ord-ca27fcca19374cbf84b6f6771e5cf097
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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