Methanol → HCID 53975795, compound

HRID 1378564Notes

Reaction equation

HRID 1378564 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=O.[Cl:20][C:21]1C=C[C:24]([C:25](N)=S)=[CH:23][CH:22]=1.CO.[S:32]1[CH:36]=[CH:35]N=C1.C(#[N:39])C>>[Cl:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:35]=1[C:36]1[S:32][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:11])[N:39]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 6342AcetonitrileHCID 9256ThiazoleHCID 27348264-ChlorothiobenzamideHCID 54543492HCID 54543492, compound

Product 1

HCID 53975795HCID 53975795, compoundYield 27%

Procedure

A solution of the bromoketone intermediate from Step 3 (0.68 g, 2.03 mmol) and 4-chlorothiobenzamide (0.34 g, 1.98 mmol) in 10 mL of acetonitrile was heated to reflux for 16 hours. The solution was cooled to room temperature and poured into 30 mL of methanol, chilled with an ice bath whereupon crystals of pure thiazole formed which were isolated by filtration and air dried to afford the desired thiazole (220 mg, 27%): mp 116°-119° C. 1H NMR (CDCl3) 300 MHz 8.33 (m, 1H), 7.50 (m, 1H), 7.16-7.36 (m, 8H), 7.12 (d, J=8.7 Hz, 2H), 2.46 (s, 3H), 2.18 (s, 3H). Mass spectrum: M+ =407.

Workup

  1. temperatureto reflux for 16 hours
  2. customformed which
  3. customwere isolated by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-2009d58cc9b3487c991f3f609c0fd3aa
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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