Carbon Dioxide → HCID 19100722, compound

HRID 1974965Notes

Reaction equation

HRID 1974965 reaction equation
[ClH:1].[NH2:2][C:3]1[S:4][C:5]([CH:11]([CH3:13])[CH3:12])=[CH:6][C:7]=1C(O)=O.C(=O)=O>C(O)CC>[ClH:1].[NH2:2][C:3]1[S:4][C:5]([CH:11]([CH3:13])[CH3:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 150855502-Amino-5-isopropyl-thiophene-3-carboxylic acid

Product 1

HCID 19100722HCID 19100722, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

Concentrated hydrochloric acid (125 ml) was heated to 60° C. with stirring, and a solution of 2-amino-5-isopropylthiophene-3-carboxylic acid (18.52 g, 0.1 mol) in 200 ml of n-propanol was added dropwise while the temperature was raised gradually to 80° C. A slow evolution of carbon dioxide, subsiding after 2 hours was observed. The mixture was evaporated in vacuo, and stripped five times with 200 ml of propanol to remove water. The residue was dissolved in 25 ml of propanol, and reprecipitated by the addition of 300 ml of tetrahydrofuran. After stirring overnight the precipitate was filtered off to yield 9.23 g (52%) of 2-amino-5-isopropylthiophene hydrochloride melting with destruction at 152°-153° C. 1H-NMR (DMSO-d6, δ): 1.2 (d, 6H), 3.2 (m, 1H), 6.7 (d, 1H), 6.8 (d, 1H).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto remove water
  3. dissolutionThe residue was dissolved in 25 ml of propanol
  4. customreprecipitated by the addition of 300 ml of tetrahydrofuran
  5. stirringAfter stirring overnight the precipitate
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-b71f376b77e54b24830eec16d0933da5
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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