Hydrochloric Acid → HCID 178468827, compound

HRID 620235Notes

Reaction equation

HRID 620235 reaction equation
[C:1]([CH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)#[N:2].C([Sn]([N:28]=[N+:29]=[N-:30])(CCCC)CCCC)CCC.Cl>COCCOC.CO>[NH:28]1[C:1]([CH2:3][C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=2)=[N:2][N:30]=[N:29]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 11989373ethyl 4-(cyanomethyl)benzoate

Product 1

HCID 178468827HCID 178468827, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 4-cyanomethylbenzoate (approximately 8 g) was dissolved in DME (10 ml). The solution was added tris(n-butyl)tin azide (5 ml) and the resultant solution was stirred and heated at 85° C. overnight. The solution was cooled to room temperature. The cooled solution was diluted with methanol then acidified with 1N hydrochloric acid. The acidified mixture was stirred for one hour then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated in vacuo.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthen partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a561e537421461a8231b4ad5f12dbd9
Source dataset
uspto-grants-1989_04
Patent number
US04820723

Reaction notes

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