Ethanol → HCID 178468665, compound

HRID 129837

Reaction equation

HRID 129837 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(C(=O)CBr)[CH:10]=[CH:9][N:8]=[N:7]1)=[O:5])[CH3:2].[C:15]([NH2:23])(=[S:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.[CH2:24](O)[CH3:25].C(=O)(O)[O-].[Na+]>O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:24]2[N:23]=[C:15]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[S:22][CH:25]=2)[NH:8][N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 737155ThionicotinamideHCID 540389643-(2-Bromoacetyl)pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 178468665HCID 178468665, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(2-bromoacetyl)pyrazole-3-carboxylic acid ethyl ester (7.00 g), thionicotinamide (3.51 g), and ethanol (50 ml) was refluxed for 16 hours. The resulting mixture was poured into 400 ml of water, and neutralized with 10 g of sodium bicarbonate. Filtration afforded 5.82 g of 3-ethoxycarbonyl-5-(2-(3-pyridinyl)thiazol-4-yl)pyrazole as yellow solids, mp 105°-107° C. NMR: 1.43 (t, 3H), 4.44 (q, 2H), 7.26 (s, 1H, 5-thiazolyl H), 7.70 (s, 1H, 4-pyrazolyl H), 7.42, 8.30, 8.73, 9.27 (4 m, 4H, pyridinyl H's).

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationFiltration

Sources & evidence

ORD record
ord-8328254a7a634a97b271ef2c9be3aadf
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Linked notes

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