Triethylamine → HCID 22290959, compound

HRID 967701Notes

Reaction equation

HRID 967701 reaction equation
C(N(CC)CC)C.[N:8]#[C:9]Br.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([OH:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18]>CC(C)=O>[O:22]([C:15]1[CH:14]=[CH:13][C:12]([Cl:11])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18])[C:9]#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 22290959HCID 22290959, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-20 °C

Procedure

At −20° C., 20.0 g (0.198 mol) of triethylamine were added with stirring to 21.0 g (0.198 mol) of cyanogen bromide in 200 ml of acetone. After 5 min, 36.9 g (0.198 mol) of methyl 5-chloro-2-hydroxybenzoate were added, and the mixture was stirred at −20° C. for 30 min. The mixture was filtered, the filter was washed with 200 ml of acetone and the combined organic phases were concentrated under reduced pressure. This gave 34.4 g of the title compound as a yellow solid which was directly reacted further.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with 200 ml of acetone
  3. concentrationthe combined organic phases were concentrated under reduced pressure
  4. customThis gave 34.4 g of the title compound as a yellow solid which was directly reacted further

Sources & evidence

ORD record
ord-42a162d563164ef0bf6c9ed3407a33c0
Source dataset
uspto-grants-2005_10
Patent number
US06956034B2

Reaction notes

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