Isopropylamine → 2-(4-nitro-1H-pyrazol-1-yl)-N-(propan-2-yl)acetamide

HRID 929920Notes

Reaction equation

HRID 929920 reaction equation
C(Cl)(=O)C(Cl)=O.[N+:7]([C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]([OH:18])=O)[CH:14]=1)([O-:9])=[O:8].C(N(CC)CC)C.[CH:26]([NH2:29])([CH3:28])[CH3:27]>CN(C=O)C.ClCCl.C1COCC1>[CH:26]([NH:29][C:16](=[O:18])[CH2:15][N:13]1[CH:14]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=[N:12]1)([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 12834772-(4-nitro-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 15046362-(4-nitro-1H-pyrazol-1-yl)-N-(propan-2-yl)acetamideYield 72.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (29.6 g, 234 mmol) and DMF (several drops) were added to a stirred mixture of 2-(4-nitro-1H-pyrazol-1-yl)acetic acid (20 g, 117 mmol) in dichloromethane (200 mL) and stirred at room temperature for 5 h. The solvent was then removed in vacuo and the residue was diluted with THF (100 mL). This solution was added to a stirred solution of triethylamine (23.7 g, 234 mmol) and iso-propylamine (10.4 g, 176 mmol) in THF (200 mL) and the reaction was stirred at room temperature overnight. The solvent was removed in vacuo and the residue diluted with 1M hydrochloric acid to pH <4. The solid was filtered, washed with 1M hydrochloric acid and dried in a vacuum oven to afford N-isopropyl-2-(4-nitro-1H-pyrazol-1-yl)acetamide as a yellow solid (18 g, 84.8 mmol).

Workup

  1. customThe solvent was then removed in vacuo
  2. additionthe residue was diluted with THF (100 mL)
  3. stirringthe reaction was stirred at room temperature overnight
  4. customThe solvent was removed in vacuo
  5. additionthe residue diluted with 1M hydrochloric acid to pH <4
  6. filtrationThe solid was filtered
  7. washwashed with 1M hydrochloric acid
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-aa50d836ad554612a53f568e40787e2c
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

Loading…