Trifluoroacetic acid → HCID 13649669, compound

HRID 280658Notes

Reaction equation

HRID 280658 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:10]([Cl:22])[CH:9]=2)[N:5]=[N:4][C:3]=1[C:23]([NH2:25])=[O:24].FC(F)(F)C(O)=[O:29].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:29])=[C:10]([Cl:22])[CH:9]=2)[N:5]=[N:4][C:3]=1[C:23]([NH2:25])=[O:24]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 13649668HCID 13649668, compound

Product 1

HCID 13649669HCID 13649669, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 5-amino-1-(3-chloro4-[4-chlorophenylthio]benzyl)-1,2,3-triazole-4-carboxamide (475 mg, 1.20 mmol) in methanol (160 ml) was treated with trifluoroacetic acid (278 μl, 411 mg, 3.61 mmol), warmed until homogeneous, and cooled to ambient temperature. To this solution was added m-chloroperbenzoic acid (244 mg of 85% technical grade, 1.20 mmol), the mixture was stirred 75 minutes, an additional portion of m-chloroperbenzoic acid (33.1 mg of 85% technical grade, 0.163 mmol) was added, and the mixture was stirred an additional 45 minutes. The mixture was treated with 2.5N aqueous sodium hydroxide (2.5 ml), stirred until crystallization commenced, concentrated to approximately 40 ml under vacuum at 30° C., and chilled to 0° C. The precipitate was filtered, washed with methanol, and dried to afford 410 mg (83%) of 5-amino-1-(3-chloro-4-[4-chlorophenylsulfinyl]benzyl)-1,2,3-triazole- 4-carboxamide, m.p. 237°-238° C.

Workup

  1. temperaturewarmed until homogeneous, and
  2. stirringthe mixture was stirred an additional 45 minutes
  3. stirringstirred until crystallization
  4. concentrationconcentrated to approximately 40 ml under vacuum at 30° C.
  5. temperaturechilled to 0° C
  6. filtrationThe precipitate was filtered
  7. washwashed with methanol
  8. customdried

Sources & evidence

ORD record
ord-6a1bd0774fb54e688ef9bc4cfa848267
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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