Hydrochloric Acid → HCID 14719508, compound

HRID 465915Notes

Reaction equation

HRID 465915 reaction equation
C(Cl)(=O)OCC.[OH:7][C:8]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][NH2:28].Cl>C(Cl)Cl.C(N(CC)CC)C>[OH:7][C:8]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][C:9]=1[C:10]([NH:28][CH2:27][C:23]1[S:22][CH:26]=[CH:25][CH:24]=1)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 34005(2-Thienylmethyl)amineHCID 14719507HCID 14719507, compound

Product 1

HCID 14719508HCID 14719508, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere, a solution of ethyl chlorocarbonate (7.65 ml) in methylene chloride (90 ml) was cooled to -15° C., and to the solution was added dropwise a solution of 2-hydroxy-3-n-propyl-4-methoxybenzoic acid (8 g) and triethylamine (11.1 ml) in methylene chloride (160 ml) for 30 minutes, and the mixture was agitated for another 15 minutes. 2-thiophenemethylamine (4.7 ml) was added to the mixture and the mixture was agitated for 3 hours while the temperature of the mixture was elevated to 0° C. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with a mixed solution of saturated aqueous solution of sodium chloride and saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and concentrated in evacuated atomosphere. The residue was dissolve in methanol (100 ml), and the solution was cooled to 0° C. The solution was added to 8.5% aqueous solution of sodium hydroxide (50 ml) and the mixture was agitated at room temperature for 4.5 hours. The reaction mixture was acidified by adding 6N aqueous hydrochloric acid thereto, and extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in evacuated atomosphere. The residue was subjected to column chromatography using silica gel, and there was obtained N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)-2-thiophenemethylamine (5.7 g) from fractions eluted with n-hexane-methylene chloride (2:1).

Workup

  1. stirringthe mixture was agitated for 3 hours while the temperature of the mixture
  2. customwas elevated to 0° C
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with a mixed solution of saturated aqueous solution of sodium chloride and saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in evacuated atomosphere
  7. dissolutionThe residue was dissolve in methanol (100 ml)
  8. additionThe solution was added to 8.5% aqueous solution of sodium hydroxide (50 ml)
  9. stirringthe mixture was agitated at room temperature for 4.5 hours
  10. additionby adding 6N aqueous hydrochloric acid
  11. extractionextracted twice with ethyl acetate
  12. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated in evacuated atomosphere

Sources & evidence

ORD record
ord-e49f1269c12e4e96aba9413e1f4a6f1f
Source dataset
uspto-grants-1992_10
Patent number
US05155106

Reaction notes

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