Tetrahydrofuran → HCID 57266132, compound

HRID 1003747Notes

Reaction equation

HRID 1003747 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.[C:14](=[O:19])=[N:15]C(Cl)=O.C1C[O:23][CH2:22]C1>>[Br:2][CH2:3][CH2:4][CH2:5][N:6]([N:15]=[C:14]=[O:19])[CH:22]=[O:23]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 787013-Bromopropylamine hydrobromideHCID 119708Isocyanatocarbonyl chloride

Product 1

HCID 57266132HCID 57266132, compound

Conditions

Temperature
-78 °C

Procedure

To 3-bromo-1-propylamine hydrobromide (1.0 g, 4.56 mmol) in THF (20 mL) was added triethylamine (2.31 g, 22.8 mmol). The mixture was cooled to -78° C., triturated with N-(chlorocarbonyl)isocyanate (723 mg, 6.85 mmol) and stirred for 10 min. It was then concentrated, and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated to give, in quantitative yield, the crude product which was used without purification.

Workup

  1. concentrationIt was then concentrated
  2. customthe residue was partitioned between EtOAc and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give, in quantitative yield
  7. customthe crude product which was used without purification

Sources & evidence

ORD record
ord-1c5bc66c5e8349f7bde5df428ff0b3b3
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

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