Potassium Carbonate → HCID 15684612, compound

HRID 728153Notes

Reaction equation

HRID 728153 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([CH2:21]O)[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1.S(Cl)([Cl:27])=O.C(=O)([O-])[O-].[K+].[K+]>>[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([CH2:21][Cl:27])[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 15684564HCID 15684564, compound

Product 1

HCID 15684612HCID 15684612, compound

Procedure

A mixture of 2-amino-6-[2-(7-hydroxymethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.5 g) and thionyl chloride (5 ml) was stirred for 40 minutes under ice-cooling. The reaction mixture was poured into ice-water and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate solution. The aqueous mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated and triturated with diethyl ether to give 2-amino-6-[2-(7-chloromethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.42 g).

Workup

  1. temperaturecooling
  2. extractionThe aqueous mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-0b97635737b44b38b8542e3ff5c77f72
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

Loading…