Hydrochloric Acid → HCID 178499470, compound

HRID 1600796Notes

Reaction equation

HRID 1600796 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].[NH4+].[Cl-].Cl>O.CN(C=O)C>[NH:16]1[C:1]([CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2)=[N:2][N:18]=[N:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21830913HCID 21830913, compound

Product 1

HCID 178499470HCID 178499470, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of methyl 4-(cyanomethoxy)phenylacetate (2.5 g, 12 mmol), NaN3 (0.87 g), NH4Cl (0.72 g, 13 mmol) and DMF (20 ml) was heated at 125° C. for 24 hours. The reaction mixture was cooled, water was added and the mixture was stripped in vacuo without allowing the solution to be stripped to dryness. This procedure was repeated (2×) and then water was added, followed by 2N HCl. The product crystallized from the solution and was collected by filtration, and washed with water and air dried to afford 1.7 g (60%) of methyl 4-(5-tetrazolylmethoxy)phenylacetate.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe product crystallized from the solution
  3. filtrationwas collected by filtration
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-7cee67dc0744491bbbc6a15cd84060a9
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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