Hydrochloric Acid → HCID 86722772, compound

HRID 2203392

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[Br:15][C:16]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:17]=1[CH:18]=O.[C:26]([O:32][CH3:33])(=[O:31])[CH2:27][C:28]([CH3:30])=O.C[Si](OP([O-])([O-])=O)(C)C.Cl>C1COCC1>[CH3:33][O:32][C:26]([C:27]1[CH:18]([C:17]2[CH:20]=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:16]=2[Br:15])[NH:12][C:10](=[S:11])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[C:28]=1[CH3:30])=[O:31]

Participants

Conditions

Temperature: 75 °C

Procedure

3-Trifluoromethylphenylthiourea (12.8 g, 87 mmol), 2-bromo-4-cyanobenzaldehyde (18.3 g, 87 mmol), and methyl acetoacetate (10.4 mL, 96 mmol) were dissolved in THF (300 mL) under an atmosphere of N2 and then trimethylsilylphosphate (18 g) in THF (50 mL) was added, and the mixture heated at 75° C. After 17 hours the reaction mixture was allowed to cool, poured onto 0.5 M HCl (600 mL) and stirred for 30 minutes. The mixture was extracted into EtOAc. The organic phase was washed with water, then brine and dried (Na2SO4) before being concentrated in vacuo. The resulting solid was triturated with Et2O (50 mL), filtered and the solid collected to yield the title compound as a white solid (22.2 g).

Workup

temperatureto cool
extractionThe mixture was extracted into EtOAc
washThe organic phase was washed with water
dry with materialbrine and dried (Na2SO4)
concentrationbefore being concentrated in vacuo
customThe resulting solid was triturated with Et2O (50 mL)
filtrationfiltered
customthe solid collected

Sources & evidence

ORD record: ord-af3de181f6d14fd1a0a3cbdb6e80e403
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365577B2

Linked notes

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