3-Fluoroaniline → HCID 86712756, compound

HRID 1754547Notes

Reaction equation

HRID 1754547 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(C(C)C)C(C)C)C.[C:18]1(=[CH:22][C:23](Cl)=[O:24])[CH2:21][CH2:20][CH2:19]1>ClCCl>[C:18]1(=[CH:22][C:23]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=2)=[O:24])[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 81531DiisopropylethylamineHCID 86712757HCID 86712757, compound

Product 1

HCID 86712756HCID 86712756, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g (13.50 mmol) of 3-fluoroaniline were dissolved in 20 ml of dichloromethane and treated with 5.19 g (29.7 mmol) of N-ethyl-N-isopropylpropan-2-amine. Within 10 min 12.82 g (16.20 mmol) of 2-cyclobutylideneacetyl chloride were added at 0° C. and the solution was stirred overnight at room temperature. The mixture was poured on ice water and extracted 2× with dichloromethane. The combined organic phases were washed once with saturated sodium chloride solution, dried with MgSO4 and evaporated in vacuo. The crude oil was treated with heptane and decanted twice, redissolved in ether-dichloromethane and treated with heptane till crystallization, yielding 2.2 g (77%) of a beige solid.

Workup

  1. additionThe mixture was poured on ice water
  2. extractionextracted 2× with dichloromethane
  3. washThe combined organic phases were washed once with saturated sodium chloride solution
  4. dry with materialdried with MgSO4
  5. customevaporated in vacuo
  6. additionThe crude oil was treated with heptane
  7. customdecanted twice
  8. dissolutionredissolved in ether-dichloromethane
  9. additiontreated with heptane till crystallization

Sources & evidence

ORD record
ord-de6bd1e8cb82485b996dcb0d572bf3ff
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

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