3,5-Dichlorophenyl isocyanate → HCID 52912059, compound

HRID 1892270Notes

Reaction equation

HRID 1892270 reaction equation
[NH:1]([C:3]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[Cl:16][C:17]1[CH:18]=[C:19]([N:24]=[C:25]=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1>>[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

3

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 67083086HCID 67083086, compound

Product 1

HCID 52912059HCID 52912059, compound

Procedure

A solution of 2-hydrazinyl-4-isopropylquinoline (97 mg, 0.48 mmol) and 91 mg (1.0 eq) of 3,5-dichlorophenyl isocyanate was reacted as outlined in Scheme 1 above to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.29 (d, J=6.74 Hz, 6 H) 3.53-3.71 (m, 1 H) 6.83 (s, 1 H) 7.09 (t, J=1.90 Hz, 1 H) 7.28 (td, J=7.47, 1.46 Hz, 1 H) 7.45-7.62 (m, 2 H) 7.69 (br. s., 2 H) 7.94 (d, J=7.62 Hz, 1 H) 8.50 (br. s., 1 H) 8.70 (s, 1 H) 9.23 (br. s., 1 H).

Sources & evidence

ORD record
ord-58ff8d01d9774bfda71c03c1cb132fe4
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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