Formic Acid → HCID 86761598, compound

HRID 883179Notes

Reaction equation

HRID 883179 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:12][CH2:13][CH3:14])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:15]([O-])(=[O:17])C.[NH4+].C(O)=O>O>[CH:15]([NH:1][C:2]1[S:3][C:4]([CH2:12][CH2:13][CH3:14])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:17]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 517165Ammonium AcetateHCID 3399457ethyl 2-amino-5-propylthiophene-3-carboxylate

Product 1

HCID 86761598HCID 86761598, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
137.5 °C

Procedure

A mixture of compound 2c [Formula 2 wherein R1=COOEt, R2=H and R3=Pr] (5.0 g, 0.023 mol), ammonium acetate (1.80 g, 0.023 mol) and formic acid (17.70 mL, 0.469 mol) was stirred at 135-140° C. for 7 h, cooled to room temperature, diluted with water (250 mL), extracted with ethyl acetate (3×150 mL), dried over Na2SO4, concentrated and purified by column chromatography to give pure compound of Formula (3c); 5.27 g; Yield: 95%; 1H NMR (200 MHz, CDCl3): δ 0.96 (t, J=7 Hz, 3H), 1.38 (t, J=7 Hz, 3H), 1.59-1.76 (m, 2H), 2.69 (t, J=8 Hz, 2H), 4.33 (q, J=7 Hz, 2H), 6.88 (s, 1H), 8.49 (s, 1H) 10.93 (bs, 1H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-198b9e5abd4f4a9596446c07c1eecfe2
Source dataset
uspto-grants-2012_08
Patent number
US08236840B2

Reaction notes

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