2-Amino-2-methyl-1-propanol → HCID 22336254, compound

HRID 225990Notes

Reaction equation

HRID 225990 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[C:10](Cl)=[O:11]>C(Cl)Cl.O>[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[C:10]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:11]

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 874382,6-Difluorobenzoyl chloride

Product 1

HCID 22336254HCID 22336254, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 2-amino-2-methylpropanol (10.1 g, 113.3 mmol) in CH2Cl2 (75 mL) under nitrogen was added dropwise a solution of 2,6-difluorobenzoyl chloride (10.0 g, 56.6 mmol) in CH2Cl2 (50 mL). The reaction mixture was then warmed to room temperature and stirred overnight. The reaction mixture was diluted with H2O, and the aqueous phase was extracted with CH2Cl2, dried (MgSO4) and concentrated. Purification via trituration with hexanes afforded 12.05 g (93%) of the amide, a white solid. 1H NMR (400 MHz, CDCl3) δ 1.41 (s, 6 H), 3.66-3.75 (m, 2 H), 3.77-3.87 (m, 1 H), 5.94 (s, 1 H), 6.90-6.99 (m, 2 H), 7.31-7.41 (m, 1 H).

Workup

  1. extractionthe aqueous phase was extracted with CH2Cl2
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification via trituration with hexanes

Sources & evidence

ORD record
ord-d9df72d6c4884b788c138230cfeb6633
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

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