Ammonia → HCID 10488080, compound

HRID 618630Notes

Reaction equation

HRID 618630 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.NC(N)=[S:16].N.Cl>C(O)C>[C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][SH:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 561788(6-Bromohexyl)benzeneHCID 2723790Thiourea

Product 1

HCID 10488080HCID 10488080, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.0 g (62.2 mmol) 1-bromo-6-phenyl-hexane (described in the unexamined laid-open patent application of the int. Appl. PCT/EP95/04413) dissolved in 40 ml ethanol was added under a nitrogen atmosphere to a solution of 7.10 g (93.3 mmol) thiourea in 30 ml ethanol. After boiling for 7 hours at reflux temperature, it was allowed to cool to room temperature, admixed with 33 ml concentrated ammonia and heated for 4 h to reflux. Subsequently it was acidified to pH 1 with 15 ml concentrated HCl. It was extracted three times with 200 ml ether each time, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and the solvent was removed in a vacuum. The residue was taken up in dichloromethane, the solid was suction filled, rewashed with dichloromethane and the filtrate was evaporated in a vaccum. 9.80 g (82%) 13 as a colourless oil.

Workup

  1. temperatureat reflux temperature, it
  2. temperatureheated for 4 h
  3. temperatureto reflux
  4. extractionIt was extracted three times with 200 ml ether each time
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed in a vacuum
  8. additionfilled
  9. customthe filtrate was evaporated in a vaccum

Sources & evidence

ORD record
ord-5e0175bef9144212bb074ab704820e6a
Source dataset
uspto-grants-1999_09
Patent number
US05955452

Reaction notes

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