Water → HCID 14547559, compound

HRID 1722821Notes

Reaction equation

HRID 1722821 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.B(Cl)(Cl)Cl.[CH3:18][S:19][C:20]#N.[OH2:22]>C1(C)C=CC=CC=1>[CH3:18][S:19][C:20]([C:10]1[C:11]2[NH:12][C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 11168Methyl thiocyanateHCID 25135Boron Trichloride

Product 1

HCID 14547559HCID 14547559, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1.67 g of carbazole in 10 ml of toluene was added 5.4 ml of a solution of 2.04M boron trichloride--toluene under ice-cooling, and the mixture was refluxed with heating on an oil bath for 1 hr. After ice-cooling, the mixture was mixed with 1 ml of methyl thiocyanate, stirred at room temperature for 3 hr., mixed with 30 ml of water and refluxed with heating on an oil bath for 1 hr. The product was extracted with toluene, dried over anhydrous magnesium sulfate, chromatographed on a column of 10 g of silica gel and eluted with toluene. The eluate was concentrated to give 2.16 g of the crude crystals. Recrystallization from methylene chloride--ether gave 2.08 g of carbazol-1-thiocarboxylic acid S-methyl ester melting at 122°-123° C. as crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating on an oil bath for 1 hr
  3. temperatureAfter ice-cooling
  4. temperaturerefluxed
  5. temperaturewith heating on an oil bath for 1 hr
  6. extractionThe product was extracted with toluene
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customchromatographed on a column of 10 g of silica gel
  9. washeluted with toluene
  10. concentrationThe eluate was concentrated
  11. customto give 2.16 g of the crude crystals
  12. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-be3e48a2bda043c1b3c9f132fb027ec7
Source dataset
uspto-grants-1989_08
Patent number
US04857645

Reaction notes

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