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

HRID 870881Notes

Reaction equation

HRID 870881 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]>O>[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

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 117703963-Cyano-4-isobutoxybenzothioamide

Product 1

HCID 98845495-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl esterYield 90.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Water (30 mL) was placed into a round bottom flask and 3-cyano-4-isobutoxybenzothioamide (3.0 g) was added, followed by addition of ethyl-2-chloroacetoacetate (2.52 g). The mixture was heated to reflux and maintained until reaction completion. After the reaction was completed, the mass was cooled to about 25° C. and maintained for about 20 minutes. The mass was then filtered. The wet solid was dried at about 60° C. to a constant weight to yield 4.0 g of the title compound. Purity by HPLC: 95.74%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained until reaction completion
  4. temperaturemaintained for about 20 minutes
  5. filtrationThe mass was then filtered
  6. customThe wet solid was dried at about 60° C. to a constant weight

Sources & evidence

ORD record
ord-3e36d188c1b34488a7d3f5995aee45dd
Source dataset
uspto-grants-2015_03
Patent number
US08969582B2

Reaction notes

Loading…