Phosphorus oxychloride → HCID 21317979, compound

HRID 263024Notes

Reaction equation

HRID 263024 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[CH2:16]([CH:18]1[CH2:25][C:21]2[S:22][CH:23]=[CH:24][C:20]=2[CH2:19]1)[CH3:17]>O>[CH2:16]([CH:18]1[CH2:25][C:21]2[S:22][C:23]([CH:14]=[O:15])=[CH:24][C:20]=2[CH2:19]1)[CH3:17]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 21317977HCID 21317977, compound

Product 1

HCID 21317979HCID 21317979, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
30 °C

Procedure

115 cm3 of phosphorus oxychloride and 155 cm3 of N-methylformanilide are stirred for 30 minutes at ambient temperature. 228 g of 5-ethyl-4,5-dihydro-6H-cyclopenta[b]thiophene, prepared as in Example 5, are added dropwise to this complex whilst the temperature is maintained at 30° C., if necessary by cooling with iced water. After the end of the addition, the reaction mixture is stirred for a further 6 hours at ambient temperature and is then poured carefully on to a mixture of water and ice. The organic products are extracted with ether. The extract is washed with water until neutral and then dried over sodium sulphate. The ether is evaporated and the residue obtained (290 g) is distilled in vacuo. This gives 205 g of 5-ethyl-4,5-dihydro-6H-cyclopenta[b]thiophene-2-carboxaldehyde as a liquid, b.p. 112°-115° C./0.6 mm Hg.

Workup

  1. additionare added dropwise to this complex whilst the temperature
  2. additionAfter the end of the addition
  3. extractionThe organic products are extracted with ether
  4. washThe extract is washed with water until neutral and
  5. dry with materialthen dried over sodium sulphate
  6. customThe ether is evaporated
  7. customthe residue obtained (290 g)
  8. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-8ff76d1190b74da19c42ee2d5f27db1e
Source dataset
uspto-grants-1979_05
Patent number
US04156000

Reaction notes

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