Chlorodifluoromethane → HCID 14014318, compound

HRID 1194627Notes

Reaction equation

HRID 1194627 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([OH:10])[N:7]=[C:6]([NH:11][CH:12]([CH3:14])[CH3:13])[N:5]=1)[CH3:2].[OH-].[K+].COCCOCCOC.Cl[CH:27]([F:29])[F:28]>O>[F:28][CH:27]([F:29])[O:10][C:8]1[N:9]=[C:4]([NH:3][CH2:1][CH3:2])[N:5]=[C:6]([NH:11][CH:12]([CH3:13])[CH3:14])[N:7]=1

Participants

6

Reactant 4

HCID 6372ChlorodifluoromethaneHCID 8150DiglymeHCID 14797Potassium HydroxideHCID 178463635HCID 178463635, compound2×

Product 1

HCID 14014318HCID 14014318, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 200 g (1.02 moles) of 2-ethylamino-4-hydroxy-6-isopropylamino-1,3,5-triazine, 454 g (8.11 moles) of potassium hydroxide, 1150 ml of diethylene glycol dimethyl ether and 1150 ml of water was vigorously stirred, and heated to 90° C. Chlorodifluoromethane gas was blown into the reaction mixture until 2-ethylamino-4-hydroxy-6-isopropylamino-1,3,5-triazine was no longer detected by thin-layer chromatography. After the reaction, the reaction mixture was cooled to room temperature, extracted with methylene chloride. The methylene chloride layer was washed with water twice or thrice, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The crude product was chromatographed on a silica gel column. The column was eluted with n-hexane/ethyl acetate (5:1) to give 58.9 g of 2-difluoromethoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine.

Workup

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride layer was washed with water twice
  5. dry with materialthrice, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe crude product was chromatographed on a silica gel column
  9. washThe column was eluted with n-hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-ff80153b410847d4914705e403cbc2e8
Source dataset
uspto-grants-1989_03
Patent number
US04816064

Reaction notes

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