Triethylamine → HCID 3753008, compound

HRID 588377

Reaction equation

HRID 588377 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].C(N1C=CN=C1)([N:13]1C=CN=C1)=O.[Cl-].[NH4+].C(N(CC)CC)C>C(Cl)Cl>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7]([NH2:13])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 6736874-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 3753008HCID 3753008, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottom flash was charged with 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid (297 g, 1.18 mol), DCM (2.97 L), and 1,1′-carbonyldiimidazole (CDI) (207 g, 97% by mass, 1.24 mol). The reaction mixture was stirred at room temperature for 45 min. Ammonium chloride (189 g, 3.53 mol) and triethylamine (498 mL, 3.53 mol) were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was suspended in H2O (˜3 L) and granulated at room temperature for 1 h. The solid was collected via filtration, washed with H2O, and dried in a vacuum oven to afford 4-iodo-1-methyl-1H-pyrazole-5-carboxamide as a colorless solid (222 g, 75% yield).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. waitgranulated at room temperature for 1 h
  4. filtrationThe solid was collected via filtration
  5. washwashed with H2O
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e3bcfb06889648cbaad8ed66c541d6c7
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Linked notes

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