Formamide → HCID 178470649, compound

HRID 1504010Notes

Reaction equation

HRID 1504010 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].[CH:22]([NH2:24])=O>>[OH:8][C:7]1[C:6]2[C:5]3[CH2:12][CH:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=[CH:22][N:24]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 86695164HCID 86695164, compound

Product 1

HCID 178470649HCID 178470649, compoundYield 52%

Procedure

A solution of ethyl 2-amino-5-(2-ethoxy-2-oxoethyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (20.68 g, 66.41 mmol, 1.00 equiv) in 100 mL of formamide was stirred overnight at 180° C. in an oil bath. After the starting material disappeared, the reaction was cooled to room temperature, quenched with water and extracted with 3×200 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2) to afford the corresponding ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (10.10 g, 52%) as yellow oil. MS: m/z 293 (M+H)+.

Workup

  1. customquenched with water
  2. extractionextracted with 3×200 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3b2ed4f73a2244f881a6c895419ee363
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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