Water → HCID 58065274, compound

HRID 1627427Notes

Reaction equation

HRID 1627427 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:3]=1.O.[NH2:25][NH2:26].O>O1CCOCC1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:4]2[N:5]=[C:6]([C:8]3[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=3[F:15])[N:7]=[C:2]([NH:25][NH2:26])[N:3]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 58065298HCID 58065298, compound

Product 1

HCID 58065274HCID 58065274, compoundYield 165.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

General Method 1A Step 3A.1 part a. To a solution of 151 mg (0.4 mmol) of triazine (XXVI) in 4 mL of 1,4-dioxane was quickly added 100 uL (2 mmol) of hydrazine monohydrate. The reaction was stirred at room temperature for 12 hours and 30 mL of water was added and the mixture stirred for an additional 30 minutes. The resultant solid was collected by filtration and washed with several portions of water. The white solid was dried overnight to afford 231 mg of N-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-hydrazinyl-1,3,5-triazin-2-amine (XXVII). If the hydrazine did not form a solid that could be filtered, then the mixture was extracted three times with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to yield the hydrazine intermediate.

Workup

  1. stirringthe mixture stirred for an additional 30 minutes
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with several portions of water
  4. customThe white solid was dried overnight

Sources & evidence

ORD record
ord-16728a8cd73b4ce4a9064003cb891f44
Source dataset
uspto-grants-2014_07
Patent number
US08785630B2

Reaction notes

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