Tetrahydrofuran → HCID 178522702, compound

HRID 441652Notes

Reaction equation

HRID 441652 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1.[C:18]([C:21]1[C:29](=[O:30])[N:28]2[C:24]([S:25][C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=32)=[N:23][CH:22]=1)([OH:20])=O.[NH2:35][C:36]1[NH:40][N:39]=[N:38][N:37]=1>CN(C)C=O>[NH:37]1[C:36]([NH:35][C:18]([C:21]2[C:29](=[O:30])[N:28]3[C:24]([S:25][C:26]4[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=43)=[N:23][CH:22]=2)=[O:20])=[N:40][N:39]=[N:38]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 27258594-Oxo-4H-9-thia-1,4a-diaza-fluorene-3-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522702HCID 178522702, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 360 mg. of 1,1'-carbonyldiimidazole in 6 ml. of dry tetrahydrofuran at 140° C. is added dropwise 500 mg. of 3-carboxy-4-oxo-4H-pyrimido[2,1-b]benzothiazole in 6 ml. of dry dimethylformamide. After heating for 3 hrs., 186 mg. of 5-aminotetrazole is added, and the heating maintained for an additional 15 min. The reaction mixture is cooled and the precipitated product filtered. Recrystallization from dimethylformamide gives 200 mg. of the desired product, m.p. 330°-332° C.

Workup

  1. temperatureAfter heating for 3 hrs
  2. temperaturethe heating maintained for an additional 15 min
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe precipitated product filtered
  5. customRecrystallization from dimethylformamide
  6. customgives 200 mg

Sources & evidence

ORD record
ord-9b67cc2e5eab4594876235a38dfa0c43
Source dataset
uspto-grants-1977_08
Patent number
US04041163

Reaction notes

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