Triethylamine → HCID 20185082, compound

HRID 2309366Notes

Reaction equation

HRID 2309366 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[OH:10][C:11]([CH2:13][O:14][C:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:17][N:16]=1)=O.C(N(CC)CC)C>C(Cl)Cl>[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:11]([CH2:13][O:14][C:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17][N:16]=2)=[O:10])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 22902352HCID 22902352, compound

Product 1

HCID 20185082HCID 20185082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.33 ml N-(2-aminoethyl)-morpholine, 2.2 g 3-hydroxycarbonylmethoxy-5-phenylpyrazole and 4.3 ml triethylamine were added in this order to 3.06 g 1-methyl-2-chloropyridinum iodide in methylene chloride. The reaction mixture was then heated to boiling for 3 hours under reflux. After cooling and washing with aqueous sodium hydroxide solution, the organic phase was evaporated, and the crude product obtained was purified chromatographically. 2.3 g 3-(2-morpholinoethylaminocarbonylmethoxy)-5-phenyl-pyrazole were obtained as an oily base. IR-spectrum (as film): 3205 cm-1, 1660 cm-1.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. washwashing with aqueous sodium hydroxide solution
  5. customthe organic phase was evaporated
  6. customthe crude product obtained
  7. customwas purified chromatographically

Sources & evidence

ORD record
ord-216bf5f9f91d41bf941726204f28843b
Source dataset
uspto-grants-1987_09
Patent number
US04695566

Reaction notes

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