HCID 19100774, compound → HCID 19100699, compound

HRID 1974961Notes

Reaction equation

HRID 1974961 reaction equation
[C:1]([NH:8][C:9]1[S:10][C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]([CH2:17][CH2:18][CH3:19])[C:13]=1[N+:14]([O-])=O)([C:3](OCC)=[O:4])=[O:2]>C(O)(=O)C.[Zn]>[CH2:23]([O:22][C:20]([C:11]1[S:10][C:9]2[NH:8][C:1](=[O:2])[C:3](=[O:4])[NH:14][C:13]=2[C:12]=1[CH2:17][CH2:18][CH3:19])=[O:21])[CH3:24]

Participants

4

Reactant 1

HCID 19100774HCID 19100774, compound

Product 1

HCID 19100699HCID 19100699, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of ethyl 2-ethoxalylamino-3-nitro-4-propylthiophene-5-carboxylate (4.2 g, 11.7 mmol) and zinc dust (3.83 g, 58.6 mmol) in 57 ml of 80% aqueous acetic acid was stirred under a nitrogen atmosphere in a water bath for 1 hour. The reaction mixture was decanted from the residual zinc and poured into ice water. The precipitate was filtered off, washed with water and dried. Recrystallization from ethanol (300 ml) afforded 1.67 g (62%) of the title compound. M.p.305°-307° C. 1H-NMR (DMSO-D6,δ): 0.93 (t, 3H), 1.28 (t, 3H), 1.49 (hex, 2H), 2.96 (t, 3H), 4.26 (q, 2H), 12.06 (s, 1H), 12.54 (s, 1H).

Workup

  1. customThe reaction mixture was decanted from the residual zinc
  2. additionpoured into ice water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customRecrystallization from ethanol (300 ml)

Sources & evidence

ORD record
ord-80e94fec1e0e43e7bb86f737efe2e24c
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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