Methyl 2-chloroacetoacetate → HCID 53669583, compound

HRID 1419694Notes

Reaction equation

HRID 1419694 reaction equation
Cl[CH:2]([C:7]([CH3:9])=O)[C:3]([O:5][CH3:6])=[O:4].[C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[S:17])=[CH:14][CH:13]=1)#[N:11]>CO>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]2[S:17][C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:7]([CH3:9])[N:18]=2)=[CH:19][CH:20]=1)#[N:11]

Participants

4

Reactant 2

HCID 107332Methyl 2-chloroacetoacetateHCID 229990394-Cyanobenzene-1-carbothioamide

Product 1

HCID 53669583HCID 53669583, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of methyl 2-chloroacetoacetate (30 g, 0.19 mol) and 4-cyanothiobenzamide (21.5 g, 0.13 mol) in MeOH (250 mL) was refluxed for 15 h. The reaction mixture was then cooled to 0° C., filtered after 20 h and washed with cooled (-20° C.) MeOH and with ether. The resulting off-white solid was dried to give methyl 2-(4-cyanophenyl)-4-methylthiazole-5-carboxylate (18.7 g, 55%). If desired, additional product may be recovered by flash chromatography of the washings: mp 186°-187° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.07 (dt, Jt =1.6, Jd =8.3, 2H, arom), 7.74 (dt, Jt =1.6, Jd =8.3, 2H, arom), 3.91 (s, 3H, OMe), 2.79 (s, 3H, Me-thiazole). Analysis calculated for C13H10N2O2S: C 60.45; H 3.90; N 10.85; S 12.41. Found: C 60.31; H 3.80; N 10.53; S 11.79.

Workup

  1. temperaturewas refluxed for 15 h
  2. filtrationfiltered after 20 h
  3. washwashed
  4. temperaturewith cooled (-20° C.) MeOH
  5. customThe resulting off-white solid was dried

Sources & evidence

ORD record
ord-b371171f8f5f484e821e78aa19dd9ea8
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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