Ethyl isocyanate → HCID 67066653, compound

HRID 644862Notes

Reaction equation

HRID 644862 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([N+:17]([O-:19])=[O:18])=[C:8]([O:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)[CH:9]=1)[CH3:2].[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:20]([NH:22][C:23]([N:13]1[C:14]([CH3:16])=[CH:15][C:11]([O:10][C:8]2[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=[CH:6][C:7]=2[N+:17]([O-:19])=[O:18])=[N:12]1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 17862430HCID 17862430, compound

Product 1

HCID 67066653HCID 67066653, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Reaction of 3-(5-ethoxy-2-nitrophenyloxy)-5-methylpyrazole with ethyl isocyanate was carried out in ethyl acetate in the presence of potassium carbonate in the same manner as in Example 99, to give a yellow solid of N-ethyl-3-(5-ethoxy-2-nitrophenyloxy)-5-methylpyrazole-1-carboxamide (yield: 75.9%). mp: 73-75° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.20 (t, J=7.2 Hz, 3H), 1.44 (t, J=7.0 Hz, 3H), 2.59 (d, J=0.7 Hz, 3H), 3.35 (dq, J=5.9 and 7.2 Hz, 2H), 4.09 (q, J=7.0 Hz, 2H), 5.78 (q, J=0.7 Hz, 1H), 6.73 (d, J=2.4 Hz, 1H), 6.77 (dd, J=2.4 and 8.9 Hz, 1H), 6.81 (br s, 1H), 8.06 (d, J=8.9 Hz, 1H).

Sources & evidence

ORD record
ord-c19a4d1e7fdc4d99a9e61031860a6230
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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