Aniline → HCID 4592636, compound

HRID 1418044Notes

Reaction equation

HRID 1418044 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](Cl)=[O:8].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([NH:11][C:7]([CH:3]2[C:2]([CH3:10])([CH3:1])[C:4]2([CH3:6])[CH3:5])=[O:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 4592636HCID 4592636, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (1.60 g, 10 mmole) in CH2Cl2 (5 ml) was added dropwise to a solution of aniline (2.8 g, 30 mmole) in CH2Cl2 (10 ml), while maintaining the temperature at 10°-20° C. The reaction mixture was stirred for 6 hours at room temperature, diluted with CH2Cl2 (15 ml) and washed successively with H2O (2×10 ml), 1N HCl (2×10 ml), H2O (20 ml) saturated NaCl (2×15 ml). The organic layer was separated, dried over MgSO4, and evaporated to dryness under reduced pressure. The residue was crystallized from EtOAc/hexane to afford 1.1 g (5.07 mmole, 51%) of a white crystalline solid), m.p. 149° C.

Workup

  1. temperaturewhile maintaining the temperature at 10°-20° C
  2. washwashed successively with H2O (2×10 ml), 1N HCl (2×10 ml), H2O (20 ml) saturated NaCl (2×15 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-8ef19a5cd4814bfa9ae59057d59d367c
Source dataset
uspto-grants-1999_03
Patent number
US05880157

Reaction notes

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