Acetic Acid → HCID 178499642, compound

HRID 1054427Notes

Reaction equation

HRID 1054427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[CH:11][C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:9]1.C(O)(=O)C.[Cl:23][CH2:24][C:25](OCC)(OCC)[O:26]CC>C(#N)C>[Cl:23][CH2:24][C:25]([C:11]1[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:12]=1[OH:13])=[O:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 178499531HCID 178499531, compound

Product 1

HCID 178499642HCID 178499642, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of the above obtained methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate (Compound of Formula (IV), 0.60 g), was suspended in acetonitrile (5 mL) and glacial acetic acid (14 mg, 0.1 eq.) and 2-chloro-1,1,1-triethoxyethane (1.5 g) under nitrogen, was heated at 70° C. for 45-60 minutes. The resulting red solution was concentrated in vacuo to afford a red syrup that was washed with cyclohexane and then dried in vacuo. Due to its relative instability, no further purification of methyl [4-(chloroacetyl)-1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate was conducted (0.77 g, quantitative yield). MS (ESL): 344.3; MS (ESI−): 342.2.

Workup

  1. additionThe mixture of the
  2. concentrationThe resulting red solution was concentrated in vacuo
  3. customto afford a red syrup that
  4. washwas washed with cyclohexane
  5. customdried in vacuo
  6. customDue to its relative instability, no further purification of methyl [4-(chloroacetyl)-1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate

Sources & evidence

ORD record
ord-ac4630985f3740ed95524bccd5e4b264
Source dataset
uspto-grants-2016_07
Patent number
US09394306B2

Reaction notes

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