Triethylamine → HCID 21077851, compound

HRID 418453Notes

Reaction equation

HRID 418453 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[CH2:11](OCl)[CH2:12][CH2:13]C.CC[C:19](=[S:21])C.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([CH3:10])=[C:5]2[C:3]=1[NH:4][C:12]([CH3:13])=[C:11]2[S:21][CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27248182-Chloro-4-fluoro-5-methylanilineHCID 95486922-ButanethioneHCID 13752033Butyl hypochlorite

Product 1

HCID 21077851HCID 21077851, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-65 °C

Procedure

A stirred solution of 2-chloro-4-fluoro-5-methylaniline (1.655 g) in methylene chloride (100 ml) under nitrogen was treated at −65° C. with a solution of butylhypochlorite (1.126 g) in methylene chloride (5 ml), stirred at −65° C. for 10 min, treated at −65° C. with a solution of methylthioacetone (1.080 g) in methylene chloride (5 ml) stirred at −65° C. for 1 hour, treated at −65° C. with triethylamine (1.05 g) and allowed to reach ambient temperature. The solution was washed, dried (MgSO4) and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the sub-title compound (1.704 g).

Workup

  1. stirringstirred at −65° C. for 1 hour
  2. customto reach ambient temperature
  3. washThe solution was washed
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-30e3c6e8f87f47fdbced45e59d9b04e7
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

Loading…