Sodium Hydroxide → HCID 53942563, compound

HRID 1432892Notes

Reaction equation

HRID 1432892 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]=[C:8]2[C:12](=[O:13])[O:11][C:10]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.[OH-:15].[Na+]>CO.O.C(Cl)Cl>[C:10]([NH:9][C:8](=[CH:7][C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:12]([OH:11])=[O:13])(=[O:15])[CH3:14]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54316039HCID 54316039, compound

Product 1

HCID 53942563HCID 53942563, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution containing 4-(5-chloro-thiophen-2-ylmethylene)-2-methyl-4H-oxazol-5-one (1.5 g, 6.82 mmol) in MeOH (18 mL) is added 1.0 M NaOH (12.0 mL, 12 mmol) at ambient temperature. After 3 h, the reaction mixture is diluted with water (100 mL) and CH2Cl2 (100 mL) and the layers are separated. The basic, aqueous layer is washed with CH2Cl2 and then acidified using 1.0 M HCl (20 mL) to provide a crude solid which is collected on a Buchner funnel. Drying in vacuo provided 1.2 g (75%) of the title compound as a pale brown solid which is used without further purification. 1H NMR (300 MHz, DMSO-d6) δ2.00 (s, 3H), 7.14 (d, J=4.01 Hz, 1H), 7.38 (d, J=4.01 Hz, 1H), 7.63 (s, 1H), 9.28 (s, 1H), 12.73 (br s, 1H) ppm; MS (EI): m/z 245 (M+).

Workup

  1. customthe layers are separated
  2. washThe basic, aqueous layer is washed with CH2Cl2
  3. customto provide a crude solid which
  4. customis collected on a Buchner funnel
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-c9dc6499759e46edb300f8e2ddbca554
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…