Triethylamine → HCID 66986052, compound

HRID 1622090Notes

Reaction equation

HRID 1622090 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:19][NH2:20]>CN(C=O)C.O>[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:19][NH:20][C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 66986038HCID 66986038, compound

Product 1

HCID 66986052HCID 66986052, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butylisocyanate (2.9 mL, 25.5 mmol) followed by triethylamine (9.8 mL, 68 mmol) was added to a magnetically stirred solution of 3-bromo-4-(2-methoxyethoxymethoxy)benzyl-amine (5 g, 17 mmol) in DMF (50 mL) and the mixture was stirred at room temperature for 15 minutes. The mixture was diluted with water (10 mL) and the dilution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated by evaporation. Product was purified from the residue by chromatographic (silica gel) employing 100% ethyl acetate as eluent to give 1-[3-bromo-4-(2-methoxyethoxymethoxy)benzyl]-3-tert-butylurea (5.3 g).

Workup

  1. extractionthe dilution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customProduct was purified from the residue by chromatographic (silica gel)

Sources & evidence

ORD record
ord-4e7f26c8de934498a468a05af634c708
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

Loading…