Hydrochloric Acid → HCID 13221061, compound

HRID 1410183Notes

Reaction equation

HRID 1410183 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[N:17][NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][NH:17][NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 287909N-[(2-Methoxyphenyl)methylidene]benzenecarbohydrazonic acid

Product 1

HCID 13221061HCID 13221061, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

1.8 mL (11.4 mmol) triethylsilane was added to a solution of 1.45 g (5.7 mmol, crude product from 5.1) benzoic acid [1-(2-methoxyphenyl)methylidene]hydrazide in 10 mL trifluoroacetic acid at 0° C., then the mixture was stirred, first for 2 hr at 0° C. and then for 4 hr at room temperature. The yellow reaction solution was then combined with 120 mL 2 N HCl and extracted with methylene chloride, and the organic phase was then shaken with 1 N NaOH, dried with Na2SO4, and concentrated on a rotary evaporator. Stirring in diisopropyl ether and subsequent drying resulted in approximately 1.1 g product in the form of a white solid.

Workup

  1. waitfor 4 hr at room temperature
  2. extractionextracted with methylene chloride
  3. stirringthe organic phase was then shaken with 1 N NaOH
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated on a rotary evaporator
  6. stirringStirring in diisopropyl ether
  7. customsubsequent drying

Sources & evidence

ORD record
ord-78b119c8ec2a4fceaba06cd2546390e8
Source dataset
uspto-grants-2014_12
Patent number
US08921406B2

Reaction notes

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