Hydrochloric Acid → HCID 20311377, compound

HRID 2420247Notes

Reaction equation

HRID 2420247 reaction equation
[N:1]([CH2:4][C:5]1[S:9][C:8]([CH2:10][C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].Cl>O1CCCC1>[N:1]([CH2:4][C:5]1[S:9][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20311366HCID 20311366, compound

Product 1

HCID 20311377HCID 20311377, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-azidomethyl-2-thienylacetate (21.1 g., 0.10 mole) was dissolved in 300 ml. of tetrahydrofuran and 40 ml. of 3M hydrochloric acid was added. After heating at reflux for 6 hours the reaction mixture was cooled and the product isolated as described in Example 9 to obtain a 62% yield of oil. 1H--NMR (CDCl3), ppm. (δ): 9.0 (s, COOH), 6.85 (s, 2 aromatic-H), 4.4 (s, CH2N3), 3.75 (s, CH2COO); IR spectrum (neat, cm.-1 : 3000 (broad), 2100 (N3), 1710 (CO2H), 1680 and 1475.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 6 hours the reaction mixture
  3. temperaturewas cooled
  4. customthe product isolated

Sources & evidence

ORD record
ord-443db51751fa4ff4a989e895e05d7a7d
Source dataset
uspto-grants-1978_08
Patent number
US04110342

Reaction notes

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