Formic Acid → HCID 12926537, compound

HRID 851105Notes

Reaction equation

HRID 851105 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.C(O)=O.C([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=O.Cl>O>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 799113-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 12926537HCID 12926537, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-methyl-2-thiophenecarboxaldehyde (20 g), formic acid (6 ml) and N-formyl piperidine (44.4 ml) was heated under reflux for 12 h. Water (50 ml) and 2 M hydrochloric acid (30 ml) were added; and the aqueous solution was washed with ether. The solution was basified to pH 10 with 2 M sodium hydroxide (30 ml) and extracted with ether. The organic extract was evaporated to give a brown oil which was distilled to afford the title compound as a colourless oil (11.8 g) b.p. 70°/0.4 mm. NMR (CDCl3) 2.9,d, (1H); 3.27,d, (1H); 6.48,s, (2H); 7.6,m, (4H); 7.83,s, (3H); ca. 8.5,m, (>6H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 h
  3. washand the aqueous solution was washed with ether
  4. extractionextracted with ether
  5. extractionThe organic extract
  6. customwas evaporated
  7. customto give a brown oil which
  8. distillationwas distilled

Sources & evidence

ORD record
ord-f255129e79af4d82b0608b4099ee3bac
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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