Formamide → HCID 178518064, compound

HRID 1526493Notes

Reaction equation

HRID 1526493 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].[CH:16]([NH2:18])=O>O>[C:5]12[CH2:12][CH2:13][CH2:14][CH2:15][C:4]=1[S:3][C:2]1[N:1]=[CH:16][N:18]=[C:7]([OH:8])[C:6]2=1

Participants

4

Reactant 2

HCID 713FormamideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Product 1

HCID 178518064HCID 178518064, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Into a 100-mL round-bottom flask containing a solution of ethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (4.06 g, 18.02 mmol, 1.00 equiv) in 100 mL of formamide was stirred for 8 h at 160° C. in an oil bath under nitrogen. The reaction mixture was cooled to 0° C. and diluted with water. The solids were filtered and precipitated with ethyl acetate to provide 8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-ol (3.0 g, 81%) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationThe solids were filtered
  3. customprecipitated with ethyl acetate

Sources & evidence

ORD record
ord-33c97f8817374f12b694a71b67ed9ed8
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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