Hydrochloric Acid → HCID 58434886, compound

HRID 1909825Notes

Reaction equation

HRID 1909825 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH2:10][C:11]([O:13]CC)=O)=[O:8].CC(C)([O-])C.[K+].O.Cl>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[C:11](=[O:13])[CH2:10][NH:9][C:7]1=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 4632592HCID 4632592, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58434886HCID 58434886, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 2-thiopheneacetylaminoacetate (31.77 g, 140 mmol) in anhydrous toluene (190 mL) was added potassium tert-butoxide (20.95 g, 187 mmol). The mixture was heated to reflux for 2 hours. After cooling, it was poured into water (190 mL) and the water phase was isolated and acidified with dilute HCl to about pH 1 (˜70 mL 10% HCl). The pale brown precipitate was filtered, washed with water and dried. Finally, a pale brown solid with some dark brown chunks was obtained (23.8 g, yield 94%). 1H NMR (d6-DMSO, 500 MHz), δ=7.55 (dd, J=3.5, 1.0 Hz, 1H), 7.48 (s, 1H), 7.30 (dd, J=5.0 1.0 Hz, 1H), 7.01 (dd, J=5.0, 4.0 Hz, 1H), 3.88 (s, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationThe pale brown precipitate was filtered
  5. washwashed with water
  6. customdried
  7. customFinally, a pale brown solid with some dark brown chunks was obtained (23.8 g, yield 94%)

Sources & evidence

ORD record
ord-71d9d7c3f504410b969d00195272281b
Source dataset
uspto-grants-2013_12
Patent number
US08598448B2

Reaction notes

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