2-Amino-2-methyl-1-propanol → HCID 10263798, compound

HRID 1275907Notes

Reaction equation

HRID 1275907 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[F:7][C:8]([F:19])([F:18])[C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=O)=[CH:11][CH:10]=1>ClCCl>[CH3:5][C:2]1([CH3:6])[CH2:3][O:4][C:13]([C:12]2[CH:11]=[CH:10][C:9]([C:8]([F:7])([F:18])[F:19])=[CH:17][CH:16]=2)=[N:1]1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 676074-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 10263798HCID 10263798, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-2-methyl-1-propanol (21.4 g) in dichloromethane (100 ml) at 0C was added dropwise a solution of 4-(trifluoromethyl)benzoyl chloride (25 g). The mixture was stirred at room temperature for 16 hours, washed with 2M HCl then sodium bicarbonate solution, dried (MgSO4) and evaporated. The residue was dissolved in dichloromethane (100 ml) and treated with thionyl chloride (14 ml) at 0C. The mixture was stirred at room temperature for 2 hours and evaporated. The residue was partitioned between ethyl acetate and aqueous potassium hydroxide. The organic phase was dried (MgSO4) and evaporated. Yield 14.57 g.

Workup

  1. washwashed with 2M HCl
  2. dry with materialsodium bicarbonate solution, dried (MgSO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  5. additiontreated with thionyl chloride (14 ml) at 0C
  6. stirringThe mixture was stirred at room temperature for 2 hours
  7. customevaporated
  8. customThe residue was partitioned between ethyl acetate and aqueous potassium hydroxide
  9. dry with materialThe organic phase was dried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-0af3e3587724424d8a2ee87e9f9bde16
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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