Triethylamine → Ether methanol ammonium hydroxide

HRID 912614Notes

Reaction equation

HRID 912614 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.Br[CH2:9][C:10](N)=[O:11]>CN(C=O)C>[CH3:9][CH2:10][O:11][CH2:6][CH3:7].[CH3:10][OH:11].[OH-:11].[NH4+:3]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 696322-Bromoacetamide

Product 1

HCID 131726330Ether methanol ammonium hydroxideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (ACY) (0.78 mmol) in dry DMF (5 mL) was added triethylamine (0.94 mmol), followed by 2-bromoacetamide (0.27 mmol). The resulting mixture was heated at 80° C. overnight. After completion of the reaction, the cooled mixture was partitioned between ether and brine, and the organic phase was separated, dried (MgSO4), and the solvent removed at the rotary evaporator to yield a pale yellow gum. Flash chromatography (SiO2, ether:methanol:ammonium hydroxide (1000:4:1)) gave compound (ACZ) as a white solid. (48% yield). Compound (ACZ): purity >97% (HPLC); MS: m/z 506.2 (M+1); 1H NMR (DMSO d6): δ 1.8 (m, 2H), 2.2 (m, 4H), 2.6-2.8 (m, 6H), 5.35 (s, 2H), 7.0-7.5 (m, 16H), 7.7 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. customthe cooled mixture was partitioned between ether and brine
  3. customthe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed at the rotary evaporator
  6. customto yield a pale yellow gum

Sources & evidence

ORD record
ord-c0abf35af84c48018debbd7f8fd0290b
Source dataset
uspto-grants-2011_09
Patent number
US08026254B2

Reaction notes

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