Dibromomethane → Potassium diphenylmethyldithiocarbamate

HRID 1283681

Reaktionsgleichung

Reaktionsgleichung von HRID 1283681
[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 1 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-3f8d2385760a4777bcf761238cb68fcb
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03975528

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