Formamide → 1H-[1]benzothiolo[3,2-d]pyrimidin-4-one

HRID 1605695Notes

Reaction equation

HRID 1605695 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[NH2:10])(OC)=[O:2].CC(C)([O-])C.[K+].[CH:21]([NH2:23])=O.O>CS(C)=O.C(O)(=O)C>[OH:2][C:1]1[C:5]2[S:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[C:9]=2[N:10]=[CH:21][N:23]=1

Participants

7

Reactant 4

HCID 713FormamideHCID 962WaterHCID 874720Methyl 3-aminobenzo[b]thiophene-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 1785179271H-[1]benzothiolo[3,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-carbomethoxy-3-aminobenzothiophene (2.07 g.; 0.02 mole) and potassium t-butoxide (2.24 g.; 0.02 mole) in dimethylsulfoxide (30 ml.) is added an excess of formamide (ca 5 ml./g. of 2-carbomethoxy-3-aminobenzothiophene). This is heated to 90° C. until the reaction is complete as evidenced by thin layer chromatography (~30 minutes). The solution is cooled, poured into water, acidified with glacial acetic acid and the resultant solid is filtered. Washing with isopropyl alcohol and then ether yields a white solid, 1.76 g., m.p. 300°-301° C.

Workup

  1. customas evidenced by thin layer chromatography (~30 minutes)
  2. temperatureThe solution is cooled
  3. filtrationthe resultant solid is filtered
  4. washWashing with isopropyl alcohol
  5. customether yields a white solid, 1.76 g

Sources & evidence

ORD record
ord-9cadf86bc5cf4e4ca0583f5044099ea3
Source dataset
uspto-grants-1976_04
Patent number
US03950525

Reaction notes

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