Ethyl 2-chloroacetoacetate → 5-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

HRID 870883Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6](=[S:8])[NH2:7])#[N:2].[CH2:17]([O:19][C:20](=[O:26])[CH:21](Cl)[C:22]([CH3:24])=O)[CH3:18]>C(O)(C)C>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[S:8][C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:26])=[C:22]([CH3:24])[N:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])#[N:2]

Participants

Conditions

Temperature: 55 °C

Procedure

3-Cyano-4-isobutoxybenzothioamide (100.0 g), ethyl-2-chloroacetoacetate (91.29 g), and isopropyl alcohol (700 mL) were placed into a round bottom flask and stirred for about 30 minutes. The mixture was heated to reflux and maintained at that temperature until reaction completion. After the reaction was complete, the mass was cooled to about 55° C. and maintained for about 30 minutes. The mass was filtered at the same temperature and the solid was washed with hot isopropyl alcohol (400 mL). The wet solid was dried at about 60° C. to a constant weight to yield 156.4 g of the title compound. Purity by HPLC: 98.8%.

Workup

temperatureThe mixture was heated
temperatureto reflux
temperaturemaintained at that temperature until reaction completion
temperaturemaintained for about 30 minutes
filtrationThe mass was filtered at the same temperature
washthe solid was washed with hot isopropyl alcohol (400 mL)
customThe wet solid was dried at about 60° C. to a constant weight

Sources & evidence

ORD record: ord-fa762b92c72844138270ec54fe35c0e9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969582B2

Reaction notes

Loading…