Dimethylformamide → HCID 53752336, compound

HRID 728181Notes

Reaction equation

HRID 728181 reaction equation
[C:1]([NH:4][C:5]1[O:6][C:7]2[CH:13]=[C:12]([CH2:14][CH2:15][C:16]3[N:17]=[C:18]4[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]4[CH:25]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=O)C.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:37][N:38](C)[CH:39]=O>O>[CH3:37][N:38]([CH:1]=[N:4][C:5]1[O:6][C:7]2[CH:13]=[C:12]([CH2:14][CH2:15][C:16]3[N:17]=[C:18]4[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]4[CH:25]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)[CH3:39]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 15684587HCID 15684587, compound

Product 1

HCID 53752336HCID 53752336, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Acetamido-6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (2.20 g) was added in small portions to a solution of phosphorous oxychloride (1.79 ml) in N,N-dimethylformamide (20 ml) at ambient temperature with stirring. After being stirred for 1 hour, the mixture was diluted with water (200 ml) and stirred for an additional 30 minutes. The mixture was made alkaline with aqueous potassium carbonate and extracted with dichloromethane. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo to give dark brown amorphous powder. The crude material was chromatographed on silica gel by eluting with chloroform-methanol (50:1, V/V), followed by recrystallization from a mixture of methanol and diisopropyl]ether to give 2-dimethylaminomethyleneamino-6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.31 g).

Workup

  1. stirringAfter being stirred for 1 hour
  2. stirringstirred for an additional 30 minutes
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give dark brown amorphous powder
  8. customThe crude material was chromatographed on silica gel
  9. washby eluting with chloroform-methanol (50:1, V/V)
  10. customfollowed by recrystallization from a mixture of methanol and diisopropyl]ether

Sources & evidence

ORD record
ord-dba3d18eae1647f992f40fad893cf227
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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