Ethyl Acetate → HCID 178465555, compound

HRID 2054379Notes

Reaction equation

HRID 2054379 reaction equation
[C:1]([O:4]CC)(=[O:3])[CH3:2].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[C:16]([NH2:19])[NH:17][N:18]=1.[C:20](=[NH:25])(OCC)[CH3:21]>C(O)(=O)C>[C:1]([OH:4])(=[O:3])[CH3:2].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[C:16]([NH:19][C:20](=[NH:25])[CH3:21])[NH:17][N:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 65066Ethyl acetimidateHCID 178507276HCID 178507276, compound

Product 1

HCID 178465555HCID 178465555, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To the stirred ethyl acetate solution of 5-(2-chlorophenyl)-2H-pyrazol-3-ylamine was added the ethyl acetimidate free base solution over 10 minutes. Glacial acetic acid (140 ml, 2.42 mol) was then added over a 20-minute period while maintaining the reaction between 10 and 30° C. A precipitate began to form after approximately 15 ml of acetic acid had been added. After stirring for 5 hours, the product was collected on a course sintered glass funnel. The product on the filter was washed with ethyl aceate until the eluent was colorless. After drying overnight on the frit under a stream of air using low vacuum, intermediate I-1A-1a was obtained as an off-white, crystalline solid (543 g, 82.6%): +ESI MS (M+1) 235.1; 1H NMR (400 MHz, CD3OD) δ 7.58-7.52 (m, 2H), 7.42-7.39 (m, 2H), 6.43 (s, 1H), 2.38 (s, 3H), 1.86 (s, 3H).

Workup

  1. temperaturewhile maintaining
  2. customthe reaction between 10 and 30° C
  3. additionhad been added
  4. customthe product was collected on a course sintered glass funnel
  5. washThe product on the filter was washed with ethyl aceate until the eluent
  6. customAfter drying overnight on the frit under a stream of air

Sources & evidence

ORD record
ord-1db8fcf0494447dc990445d94e1d33b8
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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