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

HRID 2061736Notes

Reaction equation

HRID 2061736 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-5baa7534f214480187ce8b6c9a6bb328
Source dataset
uspto-grants-2012_10
Patent number
US08283373B2

Reaction notes

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