Formaldehyde → 5-(4-Chlorophenyl)-4-cyclopropyl-2-(hydroxymethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714670Notes

Reaction equation

HRID 714670 reaction equation
[CH2:1]=[O:2].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH:16]3[CH2:18][CH2:17]3)[C:12](=[O:15])[NH:13][N:14]=2)=[CH:6][CH:5]=1>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]([CH:16]3[CH2:18][CH2:17]3)[C:12](=[O:15])[N:13]([CH2:1][OH:2])[N:14]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 674118375-(4-Chlorophenyl)-4-cyclopropyl-2-(hydroxymethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7 ml of a 37% strength solution of formaldehyde in water were added to 1000 mg (4.24 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one [preparation according to WO 2007/134862 Example 36A], and the mixture was stirred at RT for 20 h. The precipitated solid was filtered off with suction and washed with water. Drying under high vacuum gave 878 mg (62% of theory) of the target compound.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with water
  3. customDrying under high vacuum
  4. customgave 878 mg (62% of theory) of the target compound

Sources & evidence

ORD record
ord-28e143ce134a42ddb060fb38ff9f199b
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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