Benzoyl chloride → HCID 22097203, compound

HRID 861540Notes

Reaction equation

HRID 861540 reaction equation
[CH3:1][O:2][CH:3]1[CH:7]([CH2:8][NH2:9])[CH2:6][CH:5]([O:10][CH3:11])[O:4]1.C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[C:19]([NH:9][CH2:8][CH:7]1[CH2:6][CH:5]([O:10][CH3:11])[O:4][CH:3]1[O:2][CH3:1])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 21710167HCID 21710167, compound

Product 1

HCID 22097203HCID 22097203, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2 g (12.4 mmol) of 2,5-dimethoxy-3-aminomethyltetrahydrofuran and 3.4 ml (24.8 mmol) of triethylamine were dissolved in 50 ml of anhydrous tetrahydrofuran. At 0° C., 1.7 g (12.4 mmol) of benzoyl chloride dissolved in 20 ml of anhydrous tetrahydrofuran were added dropwise. The mixture was stirred for 1 h and then filtered, and the filtrate was concentrated under reduced pressure. The residue was reprecipitated from ether/petroleum ether to yield 2.4 g of impure product which was used in the next step.

Workup

  1. additionwere added dropwise
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was reprecipitated from ether/petroleum ether

Sources & evidence

ORD record
ord-16153176cdfc4bc5813836f0b9ff939b
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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