Salicylaldehyde → HCID 21322966, compound

HRID 26360Notes

Reaction equation

HRID 26360 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]=[O:8])[C:4](O)=[CH:3][CH:2]=1.ClC1C([O:17][C:18](=[O:21])[NH:19]C)=C(Cl)C(Cl)=C(Cl)C=1Cl.[CH2:26](N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:26][C:4]1[C:3]([O:21][C:18](=[O:17])[NH2:19])=[CH:2][CH:1]=[CH:6][C:5]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8471Triethylamine2×HCID 21322965HCID 21322965, compound

Product 1

HCID 21322966HCID 21322966, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.1 g (0.0254 moles) of salicylic aldehyde are dissolved in 30 ml of anhydrous toluene and 8.1 g (0.025 moles) of N-methyl-carbamic acid-pentachlorophenyl-ester are added under stirring at room temperature, whereafter 2.6 g (0.0257 moles) of triethylamine are added to the mixture under stirring. During the addition of the triethylamine an elevation of the temperature of about 2°-5° C. may be observed. The reaction mixture is stirred at 25°-30° C. for 2 hours, after about 1 hour the reaction mixture becomes clear. The unreacted active ester is filtered, the toluene is removed from the filtrate and the residual oily substance is recrystallized from a three-fold amount of diisopropylether. 2-methyl-carbamoyloxy-benzaldehyde is obtained. Mp.: 128°-132° C.

Workup

  1. additionare added to the mixture
  2. stirringThe reaction mixture is stirred at 25°-30° C. for 2 hours, after about 1 hour the reaction mixture
  3. filtrationThe unreacted active ester is filtered
  4. customthe toluene is removed from the filtrate
  5. customthe residual oily substance is recrystallized from a three-fold amount of diisopropylether

Sources & evidence

ORD record
ord-aef4b367bf7948c0b26b53cd938af759
Source dataset
uspto-grants-1979_04
Patent number
US04150034

Reaction notes

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