O-Xylene → HCID 58434907, compound

HRID 1909826Notes

Reaction equation

HRID 1909826 reaction equation
C([O-])(=O)C.[NH4+:5].C1(C)C(C)=CC=CC=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:19]1[C:23](=O)[CH2:22][NH:21][C:20]1=[O:25]>O>[NH2:5][C:23]1[CH2:22][NH:21][C:20](=[O:25])[C:19]=1[C:15]1[S:14][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 517165Ammonium AcetateHCID 58434886HCID 58434886, compound

Product 1

HCID 58434907HCID 58434907, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask with a Dean-Stark distilling receiver, ammonium acetate (20.90 g, 271 mmol) and xylene (215 mL) were charged and kept at 60° C. Then 3-thiophen-2-yl-pyrrolidine-2,4-dione (19.0 g, 105 mmol) was added portionwise. The mixture was heated to reflux until there was no more water collected by the receiver (about 15 mL water) and a sticky gel was formed at the bottom. After cooling, toluene was decanted and the sticky gel was further washed by toluene and water and dried under vacuum at 80° C. Finally, a sticky gel was obtained (18.3 g, yield 99%), which can be used directly for the preparation of various compounds having one or more pyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione-3,6-diyl units. 1H NMR (d6-DMSO, 500 MHz), δ=7.23 (s, 1H), 7.22 (s, 1H), 7.10 (s, 1H), 7.00 (dd, J=5.0, 4.0 Hz, 1H), 6.77 (s, 2H), 3.82 (s, 2H).

Workup

  1. additionwere charged
  2. customkept at 60° C
  3. temperatureThe mixture was heated
  4. temperatureto reflux until there
  5. customcollected by the receiver (about 15 mL water)
  6. customa sticky gel was formed at the bottom
  7. temperatureAfter cooling
  8. customtoluene was decanted
  9. washthe sticky gel was further washed by toluene and water
  10. customdried under vacuum at 80° C
  11. customFinally, a sticky gel was obtained (18.3 g, yield 99%), which
  12. customcan be used directly for the preparation of various compounds

Sources & evidence

ORD record
ord-7a0fcfe0857449088786a82a3cc57cc6
Source dataset
uspto-grants-2013_12
Patent number
US08598448B2

Reaction notes

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