Formic Acid → HCID 18359869, compound

HRID 1376622Notes

Reaction equation

HRID 1376622 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12.[CH:11](O)=[O:12].C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[CH:11]([NH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12)=[O:12]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 23449290HCID 23449290, compound

Product 1

HCID 18359869HCID 18359869, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To the ice-cooled solution of the whole amount of the crude 7-aminomethyl-imidazo[5,1-b]thiazole in 5 ml of dichloromethane was added a mixture of 0.5 ml of formic acid and 0.5 ml of acetic anhydride which had been preliminarily sitrred and reacted at 50° C. for 10 minutes. The resulting mixture was stirred under ice-cooling for 30 minutes. To the reaction mixture were added 10 ml of water, 20 ml of dichloromethane and 5 ml of a 50% aqueous potassium carbonate solution, and the organic layer was separated. The aqueous layer was further extracted thrice with 20 ml of dichloromethane. The combined organic layer was purified by flash column chromatography on silica gel (eluted with chloroform: methanol=15:1) to give the title compound in a yield of 0.088 g (36%). NMR (CDCl3) δ: 4.53 (2H, d, J=5.8 Hz), 6.84 (1H, d, J=4.2 Hz), 6.86 (1H, br), 7.38 (1H, d, J=4.2 Hz), 7.93 (1H, s), 8.26 (1H, s).

Workup

  1. additionwas added
  2. customreacted at 50° C. for 10 minutes
  3. temperaturecooling for 30 minutes
  4. customthe organic layer was separated
  5. customThe combined organic layer was purified by flash column chromatography on silica gel (eluted with chloroform: methanol=15:1)

Sources & evidence

ORD record
ord-c15cdcff8d2e48679e79a5fb8081d1dc
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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