Water → HCID 20387948, compound

HRID 1579409Notes

Reaction equation

HRID 1579409 reaction equation
BrBr.C(Cl)(Cl)(Cl)Cl.N1C2C(=CC=CC=2)C=CC=1.[CH3:18][S:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:22][CH:21]=1.[OH2:37]>C(O)(=O)C>[CH3:18][S:19]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:22][CH:21]=1)=[O:37]

Participants

7

Reactant 5

HCID 962WaterHCID 5943Carbon Tetrachloride2×HCID 7047QuinolineHCID 24408BromineHCID 40069Carbamic acid, (4-(methylthio)phenyl)-, 3-pyridinylmethyl ester

Product 1

HCID 20387948HCID 20387948, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Quinoline-bromine complex was prepared by adding 3.2 g. (0.02 mole) of bromine in 50 ml. of CCl4 to a solution of 2.6 g. (0.02 mole) of quinoline in 50 ml. of CCl4. A yellow solid separated which was filtered off and air-dried. The yield was 3.5 g. (60%). To a solution of 2.7 g. (0.01 mole) of 3-pyridylmethyl N-(4'-methylthiophenyl)carbamate in 100 ml. of 70% aqueous acetic acid was added, portionwise, 2.7 g. (0.01 mole) of the quinoline-bromine complex. The mixture was stirred at ambient temperature for 15 min. and poured into 100 ml. of water. A negligible amount of solid formed and was removed by filtration. The filtrate was made alkaline with 25% aqueous NaOH, and a white precipitate formed which was filtered off and recrystallized from aqueous ethanol. There was obtained 0.5 g. of recrystallized product, melting at 118° - 121°C., which proved to be a mixture of two components by thin layer chromatography. The filtrate was concentrated to near-dryness, and yielded after oven drying in vacuo 1 g. of a white solid melting at 139° - 143° C. This was a 34% yield of 3-pyridylmethyl N-(4'-methylsulfinylphenyl)-carbamate.

Workup

  1. customQuinoline-bromine complex was prepared
  2. additionby adding 3.2 g
  3. customA yellow solid separated which
  4. filtrationwas filtered off
  5. customair-dried
  6. additionpoured into 100 ml
  7. customA negligible amount of solid formed
  8. customwas removed by filtration
  9. customa white precipitate formed which
  10. filtrationwas filtered off
  11. customrecrystallized from aqueous ethanol
  12. customThere was obtained 0.5 g
  13. additiona mixture of two components by thin layer chromatography
  14. concentrationThe filtrate was concentrated to near-dryness
  15. customyielded after oven
  16. customdrying in vacuo 1 g

Sources & evidence

ORD record
ord-9c300f77b865458da487d4e86c19f366
Source dataset
uspto-grants-1976_01
Patent number
US03931202

Reaction notes

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