Ethanol → N-(3-hydroxypropyl)-4,5-diphenyl-1H-pyrazole-1-acetamide

HRID 2073284Notes

Reaction equation

HRID 2073284 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19](OCC)=[O:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][CH2:25][CH2:26][CH2:27][OH:28].C(O)C>C(N(CC)CC)C.O>[OH:28][CH2:27][CH2:26][CH2:25][NH:24][C:19](=[O:20])[CH2:18][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]1

Participants

6

Reactant 3

HCID 702EthanolHCID 90863-Amino-1-propanolHCID 146995514,5-Diphenyl-1-(ethoxycarbonylmethyl)-pyrazole

Product 1

HCID 14699562N-(3-hydroxypropyl)-4,5-diphenyl-1H-pyrazole-1-acetamideYield 91.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.47 g (4.8 mmol) of ethyl 4,5-diphenyl-1H-pyrazole-1-acetate of Example 1, 0.72 g (9.6 mmol) of 3-amino-1-propanol and 0.024 g (0.24 mmol) of triethylamine was stirred at 100° C. for two hours. Five mL of ethanol was added and the solution was poured into 20 mL of water and allowed to stand 18 hours at 5° C. to crystallize. The product was filtered off, air-dried and recrystallized from 25 mL of ethyl acetate to yield 1.47 g of N-(3-hydroxypropyl)-4,5-diphenyl-1H-pyrazole-1-acetamide, mp 138°-139° C.

Workup

  1. waitto stand 18 hours at 5° C.
  2. customto crystallize
  3. filtrationThe product was filtered off
  4. customair-dried
  5. customrecrystallized from 25 mL of ethyl acetate

Sources & evidence

ORD record
ord-bbc16dfe352b454eb435335994979c6d
Source dataset
uspto-grants-1990_04
Patent number
US04916150

Reaction notes

Loading…