Dibromomethane → Potassium diphenylmethyldithiocarbamate

HRID 436627

Reaktionsgleichung

Reaktionsgleichung von HRID 436627
[C:1]1([CH:7]([N:14]=[C:15]=[S:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH-:17].[K+:18].CC(C)=O.C(O)(C)(C)C.C(Br)Br>CN(C)C=O.C(N(CC)CC)C>[C:1]1([CH:7]([NH:14][C:15](=[S:17])[S-:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[K+:18]

Komponenten

7

Edukt 4

HCID 3024DibromomethaneHCID 102109Potassium bisulfideHCID 520742Benzhydryl isothiocyanateHCID 19966414t-BuOH acetone

Produkt 1

HCID 23667332Potassium diphenylmethyldithiocarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Potassium diphenylmethyldithiocarbamate was prepared from diphenylmethyl isothiocyanate and potassium hydrosulfide in a t-butyl alcohol acetone mixture. A mixture of 29.7 g. of this salt, 26.1 g. of methylene bromide, and 10.1 g. of triethylamine in 200 ml. of dimethylformamide was stirred for about one hour keeping the initial reaction temperature below 30° C. by cooling. The mixture was poured into ice-water, partitioned into ethylene chloride, and gave 24.0 g. of crude product upon evaporation of the ethylene chloride. Purification by dry column chromatography on silica gel using 20% methylene chloride in hexane for developing gave 5.5 g. of solids which were recrystallized from isopropyl alcohol to give 4.4 g. of white crystals, m.p. 106.5°-107.5° C.

Aufarbeitung

  1. additionA mixture of 29.7 g
  2. customreaction temperature below 30° C.
  3. temperatureby cooling
  4. custompartitioned into ethylene chloride
  5. customgave 24.0 g
  6. customof crude product upon evaporation of the ethylene chloride
  7. customPurification
  8. dry with materialby dry column chromatography on silica gel using 20% methylene chloride in hexane
  9. customfor developing gave 5.5 g
  10. customof solids which were recrystallized from isopropyl alcohol
  11. customto give 4.4 g

Quellen und Nachweise

ORD-Eintrag
ord-7f3350bbf1df4667a479c36e7ae3cce7
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04009279

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