1,2-Dichloro-3-isocyanatobenzene → HCID 135972973, compound

HRID 1696558Notes

Reaction equation

HRID 1696558 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:17])[NH:12][CH:13]=[N:14]3)=[CH:9][CH:8]=2)[N:5]=[C:4]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:3]=1.[Cl:22][C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]=[C:31]=[O:32]>>[C:18]([C:4]1[CH:3]=[C:2]([NH:1][C:31]([NH:30][C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:23]=2[Cl:22])=[O:32])[N:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:17])[NH:12][CH:13]=[N:14]3)=[CH:9][CH:8]=2)[N:5]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 136347863HCID 136347863, compound

Product 1

HCID 135972973HCID 135972973, compoundYield 51%

Procedure

Using general method A, 7-(5-amino-3-t-butyl-1H-pyrazol-1-yl)quinazolin-4(3H)-one (120 mg, 0.424 mmol) and 2,3-dichlorophenylisocyanate (79 mg, 0.487 mmol) were combined to yield 1-(3-t-butyl-1-(4-oxo-3,4-dihydroquinazolin-7-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (102 mg, 51% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6): 9.41 (s, 1H), 8.79 (s, 1H), 8.25-8.23 (s, 1H), 8.16 (s, 1H), 8.08-8.02 (m, 1H), 7.82-7.75 (m, 2H), 7.32-7.30 (m, 2H), 6.46 (s, 1H), 1.30 (s, 9H). MS (ESI) m/e (M+H+) 471.0.

Sources & evidence

ORD record
ord-b7ee292514dd4bd38d0a57585bd95f39
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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