Triethylamine → HCID 59663835, compound

HRID 1677638Notes

Reaction equation

HRID 1677638 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH2:13].ClC(Cl)(O[C:18](=[O:24])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][N:35]=1>O1CCCC1>[Br:40][C:37]1[CH:38]=[CH:39][C:34]([NH:33][C:18]([NH:13][C:4]2[CH:5]=[C:6]([C:9]([F:11])([F:10])[F:12])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[O:24])=[N:35][CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 706222-Amino-5-bromopyridineHCID 94429TriphosgeneHCID 6006372-Methoxy-5-(trifluoromethyl)aniline

Product 1

HCID 59663835HCID 59663835, compoundYield 139.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.32 g of 2-methoxy-5-trifluoromethylphenylamine in 30 mL of tetrahydrofuran are added dropwise to a solution of 1.8 g of triphosgene in 180 mL of tetrahydrofuran at 0° C. 4.95 mL of triethylamine are then added and the reaction is stirred at this temperature for 10 minutes. The temperature is allowed to rise to 20° C. and the mixture is stirred for 1 hour 15 minutes. A solution of 3 g of 2-amino-5-bromopyridine in 30 mL of THF is then added dropwise. After 16 hours, the suspension is filtered and the filtrate is then concentrated under reduced pressure. The residue is taken up in a mixture of ethyl acetate and water. An insoluble white precipitate is obtained, which is filtered off, washed with ethyl acetate and then dried under vacuum. 3.3 g of a white powder of 1-(5-bromopyrid-2-yl)-3-(2-methoxy-5-trifluoromethylphenyl)urea are obtained.

Workup

  1. customto rise to 20° C.
  2. stirringthe mixture is stirred for 1 hour 15 minutes
  3. waitAfter 16 hours
  4. filtrationthe suspension is filtered
  5. concentrationthe filtrate is then concentrated under reduced pressure
  6. additionThe residue is taken up in a mixture of ethyl acetate and water
  7. customAn insoluble white precipitate is obtained
  8. filtrationwhich is filtered off
  9. washwashed with ethyl acetate
  10. customdried under vacuum

Sources & evidence

ORD record
ord-1225942c77514af894145e0778646ec8
Source dataset
uspto-grants-2011_08
Patent number
US08008322B2

Reaction notes

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