Hexane → HCID 22911973, compound

HRID 1378618Notes

Reaction equation

HRID 1378618 reaction equation
[F:1][C:2]1[C:7]([C:8]([NH2:10])=O)=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1.C(CC(C)(C)C)(C)C.CCCCCC>C1(C)C=CC=CC=1.C(O)(=O)C.C(Cl)Cl>[F:1][C:2]1[C:7]([C:8]([NH2:10])=[S:24])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14]

Participants

8

Reactant 4

HCID 8058HexaneHCID 109072,2,4-TrimethylpentaneHCID 695472,3,4,5,6-PentafluorobenzamideHCID 87949Lawesson's reagent

Product 1

HCID 22911973HCID 22911973, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of pentafluorobenzamide (5.00 g, 23.69 mmol) in toluene (60 mL) was added Lawesson's reagent (5.70 g, 14.20 mmol) and the flask fitted with a drying tube. The reaction was refluxed overnight, cooled to room temperature, and isooctane (200 mL) was added causing a precipitate to form. The suspension was filtered (gravity) and the filtrate concentrated yielding an orange oil which solidified. Flash chromatography of this oil (1:1 hexane:methylene chloride with 2% acetic acid) yielded crude pentafluorothiobenzamide as a white solid (mp 92°-93° C.) which was used without any further purification.

Workup

  1. customthe flask fitted with a drying tube
  2. temperatureThe reaction was refluxed overnight
  3. customto form
  4. filtrationThe suspension was filtered (gravity)
  5. concentrationthe filtrate concentrated
  6. customyielding an orange oil which

Sources & evidence

ORD record
ord-496e1ef0b3094303aadb96084880619a
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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