2-Amino-2-methyl-1-propanol → 4-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide

HRID 1185016Notes

Reaction equation

HRID 1185016 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17]>C(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 3200764-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 101a in DCM (200 mL) was added to a solution of 2-amino-2-methyl-1-propanol (1000 g, 10.5 mol) in CH2Cl2 (2000 mL) dropwise at 0-10° C. A white precipitate formed 5 minutes after the initial addition. The resulting slurry was stirred at room temperature overnight. The solid was removed by filtration and washed with CH2Cl2 (1000 mL). The filtrate was concentrated on by rotary evaporation to give 101b as a light yellow resin which was used in the next step without further purification.

Workup

  1. customA white precipitate formed 5 minutes after the initial
  2. additionaddition
  3. customThe solid was removed by filtration
  4. washwashed with CH2Cl2 (1000 mL)
  5. concentrationThe filtrate was concentrated on by rotary evaporation

Sources & evidence

ORD record
ord-7a78094b2f7c4d9293b97c37b5bd1675
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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