Hydrochloric Acid → HCID 4308572, compound

HRID 1604467Notes

Reaction equation

HRID 1604467 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11](Cl)=[O:12].Cl>C(Cl)Cl>[CH2:1]([NH:5][C:11]([C:7]1[O:6][CH:10]=[CH:9][CH:8]=1)=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 682422-Furancarbonyl chloride

Product 1

HCID 4308572HCID 4308572, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of n-butylamine (99 mL, 1.0 mol) in CH2Cl2 (300 mL) was added 2-furoyl chloride (33.0 mL, 0.335 mol) dropwise at 0-5° C. with stirring. The reaction mixture was stirred for additional 2 h at 0-5° C. and overnight at room temperature. The solution was poured into a mixture of wet-ice (200 g) and 37% HCl (50 mL). After separation, the organic layer was washed with 2×200 mL water, dried over Na2SO4 and filtered. Removal of solvent provided the title compound (49.59 g, 88.6% yield) as a white solid, m.p.=43.8° C. (Rf=0.53 on a silica gel plate using EtOAc as an eluant). This product was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred for additional 2 h at 0-5° C. and overnight at room temperature
  2. customAfter separation
  3. washthe organic layer was washed with 2×200 mL water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-f5e1407b98b24ce684e56a04783d057b
Source dataset
uspto-grants-1999_11
Patent number
US05994396

Reaction notes

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