Ammonia → 2-Amino-4-fluoro-6-chlorodifluoromethoxy-1,3,5-triazine

HRID 1198281Notes

Reaction equation

HRID 1198281 reaction equation
[NH3:1].F[CH:3]1[N:8]=[C:7]([F:9])[N:6]=[C:5]([Cl:10])[N:4]1[O:11][CH:12]([F:14])[F:13]>O1CCCC1>[NH2:1][CH:3]1[N:8]=[C:7]([F:9])[N:6]=[C:5]([Cl:10])[N:4]1[O:11][CH:12]([F:14])[F:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 677830682,4-Difluoro-6-chlorodifluoromethoxy-1,3,5-triazine

Product 1

HCID 677834822-Amino-4-fluoro-6-chlorodifluoromethoxy-1,3,5-triazineYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

7.8 g (0.46 mol) of ammonia were passed over the course of 45 minutes into a stirred mixture of 50.0 g (0.23 mol) of 2,4-difluoro-6-chlorodifluoromethoxy-1,3,5-triazine and 150 ml of tetrahydrofuran at -70° C. The mixture was stirred for 2 hours at -70° C. and overnight while warming to 22° C. It was concentrated under reduced pressure, washed with water and dried. The product was then loaded in methylene chloride onto a silica gel column and eluted with the same solvent. Fractions 1-8 yielded 21.5 g (43.6% of theory) of 2-amino-4-fluoro-6-chlorodifluoromethoxy-1,3,5-triazine of melting point 131°-133° C. Washing with ethyl acetate then yielded in fractions 9-14 the less soluble 2,4-diamino-6-chlorodifluoromethoxy-1,3,5-triazine (11.2 g, 23% of theory) of melting point 114° C.

Workup

  1. temperaturewhile warming to 22° C
  2. concentrationIt was concentrated under reduced pressure
  3. washwashed with water
  4. customdried
  5. washeluted with the same solvent

Sources & evidence

ORD record
ord-7c97d867003b45e7a69277675d91ed75
Source dataset
uspto-grants-1994_01
Patent number
US05280118

Reaction notes

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