Diphosgene → N-tetrahydrofurfuryl-5-methyl-3-(3-trifluoromethylphenyloxy)pyrazole-1-carboxamide

HRID 644901Notes

Reaction equation

HRID 644901 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:3]=1.Cl[C:19](OC(Cl)(Cl)Cl)=[O:20].[CH2:26]([NH2:32])[CH:27]1[O:31][CH2:30][CH2:29][CH2:28]1>>[CH2:26]([NH:32][C:19]([N:6]1[C:2]([CH3:1])=[CH:3][C:4]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)=[N:5]1)=[O:20])[CH:27]1[O:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 10426DiphosgeneHCID 253298TetrahydrofurfurylamineHCID 178624205-Methyl-3-(3-trifluoromethylphenyloxy)pyrazole

Product 1

HCID 67066650N-tetrahydrofurfuryl-5-methyl-3-(3-trifluoromethylphenyloxy)pyrazole-1-carboxamideYield 70.3%

Procedure

5-Methyl-3-(3-trifluoromethylphenyloxy)pyrazole reacted with trichloromethyl chloroformate in the same manner as in Example 198 and then reacted with tetrahydrofurfurylamine to give a white solid of N-tetrahydrofurfuryl-5-methyl-3-(3-trifluoromethylphenyloxy)pyrazole-1-carboxamide (yield: 70.3%). mp: 101-102° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.56-1.67 (m, 1H), 1.84-2.05 (m, 3H), 2.60 (s, 3H), 3.29-3.39 (m, 1H), 3.55 (ddd, J=3.8, 6.1 and 13.8 Hz, 1H), 3.70-3.90 (m, 2H), 4.00-4.10 (m, 1H), 5.74 (s, 1H), 7.21 (br s, 1H), 7.33-7.37 (m, 1H), 7.40-7.51 (m, 3H).

Sources & evidence

ORD record
ord-43ec7c3ecc8547d380026a6091bed480
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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