Triethylamine → HCID 13881148, compound

HRID 978009Notes

Reaction equation

HRID 978009 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][CH2:10][C:11](=[S:13])C.[CH2:14](N(CC)CC)C>C(Cl)Cl>[I:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:10]([CH3:9])=[C:11]2[S:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 95486922-Butanethione

Product 1

HCID 13881148HCID 13881148, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 10.9 g (91 mmole) of 5-butylhypochlorite in 40 mL of CH2Cl2 was added dropwise to a solution of 20.0 g (91 mmole) of 4-iodoaniline in 300 mL of CH2Cl2 at -70° C. After 10 min, a solution of 7.43 mL (91 mmole) of methylthioacetone in 40 mL of CH2Cl2 was added dropwise. After stirring for 90 min, 12.7 mL of triethylamine was added. The reaction was allowed to warm to room temperature. The mixture was washed with water, dried (K2CO3) and the solvent evaporated in vacuo. The residue was extracted with hot hexane. The precipitated crystals were collected to give 2.95 g (11% yield) of the title compound. The mp after recrystallization from CH2Cl2 -hexane was 95°-97° C.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried (K2CO3)
  3. customthe solvent evaporated in vacuo
  4. extractionThe residue was extracted with hot hexane
  5. customThe precipitated crystals were collected

Sources & evidence

ORD record
ord-d22bedc359f74422acab53dd31c36f33
Source dataset
uspto-grants-1987_05
Patent number
US04663334

Reaction notes

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