Hydrochloric Acid → (E)-N-cinnamyl-2-thiophenecarboxamide

HRID 982259Notes

Reaction equation

HRID 982259 reaction equation
C(N(CC)CC)C.[C:8]1([C:13](Cl)=[O:14])[S:12][CH:11]=[CH:10][CH:9]=1.[CH2:16]([NH2:25])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCCl.O>[CH2:16]([NH:25][C:13]([C:8]1[S:12][CH:11]=[CH:10][CH:9]=1)=[O:14])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 6008559cinnamylamine

Product 1

HCID 14650587(E)-N-cinnamyl-2-thiophenecarboxamideYield 51.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

(E)-N-Cinnamyl-2-thiophenecarboxamide may be obtained in the following manner: triethylamine (8 g) and then thenoyl chloride (6.5 g) are added to a solution, maintained under a nitrogen atmosphere and at a temperature in the region of 25° C., of (E)-cinnamylamine (5.3 g) in 1,2-dichloroethane (80 cc). The suspension obtained is stirred for 1 hour at a temperature in the region of 25° C. and then poured into water (80 cc). The aqueous phase is acidified to a pH in the region of 5 with 4 N aqueous hydrochloric acid solution and then extracted with 1,2-dichloroethane (2×50 cc). The combined organic phases are washed with water (2×40 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (4 kPa) at 40° C. The residue is stirred in isopropyl ether (40 cc). The solid is separated by filtration, washed with isopropyl ether (4×10 cc) and dried in the air. (E)-N-Cinnamyl-2-thiophenecarboxamide (5 g), m.p. 110° C., is thereby obtained.

Workup

  1. customThe suspension obtained
  2. extractionextracted with 1,2-dichloroethane (2×50 cc)
  3. washThe combined organic phases are washed with water (2×40 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (4 kPa) at 40° C
  7. stirringThe residue is stirred in isopropyl ether (40 cc)
  8. customThe solid is separated by filtration
  9. washwashed with isopropyl ether (4×10 cc)
  10. customdried in the air

Sources & evidence

ORD record
ord-1dc3a404473e4c2a86b8fde4579b428b
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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