Methane → HCID 12637886, compound

HRID 709345Notes

Reaction equation

HRID 709345 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:12]([O-])=O.[Na+].NC(N)=O.N(O)=O.C.[ClH:24]>O>[Cl-:24].[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([N+:6]#[N:12])[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 6

HCID 297MethaneHCID 313Hydrochloric AcidHCID 1176UreaHCID 73753-(Trifluoromethyl)anilineHCID 24529Nitrous AcidHCID 23668193Sodium Nitrite

Product 1

HCID 12637886HCID 12637886, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Carbon black (10 g of Cabot R330A67) was added to 100 ml of water and stirred using a Cowles-type blade powered by an overhead shaft-driven motor operating at 500 rpm to form a carbon black slurry. Mixing was continued for 1 hour. Meanwhile, a solution of 3-trifluoromethylbenzene diazonium chloride was prepared by dissolving 0.64 g (0.004 mol) of m-trifluoromethyl-aniline in 10 ml of water containing 1.5 ml of concentrated HCl, chilling the solution to less than about 10° C. using an ice bath, and then adding 0.3 g (0.0043 mol) of sodium nitrite in 5 ml of water. The resulting mixture was stirred cold for 30 minutes and 30 mg of urea were added to decompose any excess nitrous acid. The resulting solution was added to the carbon black slurry and stirring was continued at ambient temperature for about 3 hours. Some gas evolution was noted.

Workup

  1. additionMixing
  2. temperaturechilling the solution to less than about 10° C.
  3. stirringstirring
  4. waitwas continued at ambient temperature for about 3 hours

Sources & evidence

ORD record
ord-e26057dc06a84df981b11885aca9d740
Source dataset
uspto-grants-2015_11
Patent number
US09180654B2

Reaction notes

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