Tetrahydrofuran → HCID 20348887, compound

HRID 263197Notes

Reaction equation

HRID 263197 reaction equation
O1CCCC1.[S:6]1[CH:10]=[CH:9][C:8]2[CH:11]([N:15]=[C:16]=[S:17])[CH2:12][CH2:13][CH2:14][C:7]1=2.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CCOCC>[S:6]1[CH:10]=[CH:9][C:8]2[CH:11]([NH:15][C:16]([CH:21]3[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]3)=[S:17])[CH2:12][CH2:13][CH2:14][C:7]1=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 20348910HCID 20348910, compound

Product 1

HCID 20348887HCID 20348887, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 50 ml. of tetrahydrofuran, 5.85 grams of 4,5,6,7-tetrahydrobenzo[b]thien-4-yl isothiocyanate is stirred and 2.81 grams of piperidine is added. An exotherm is observed and the temperature rises to about 40° C. to 50° C. After 2.5 hours, the mixture is heated at reflux temperature for 3.5 hours. After stirring overnight, the mixture is evaporated to dryness to afford a sticky yellow-brown solid. Ether is added to this material and the off-white, insoluble product is collected. The crude product, 5.25 grams, melts at 102° C. to 104° C.

Workup

  1. customrises to about 40° C. to 50° C
  2. temperaturethe mixture is heated
  3. temperatureat reflux temperature for 3.5 hours
  4. customthe mixture is evaporated to dryness
  5. customto afford a sticky yellow-brown solid
  6. customthe off-white, insoluble product is collected

Sources & evidence

ORD record
ord-f3569829620e4e2585534dac35a49e06
Source dataset
uspto-grants-1979_05
Patent number
US04156670

Reaction notes

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