Hydrochloric Acid → HCID 53759908, compound

HRID 651884Notes

Reaction equation

HRID 651884 reaction equation
O[CH:2]1[C:6]2[CH:7]=[C:8]([CH3:19])[CH:9]=[C:10]([C:11]([CH3:18])([CH3:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=2[O:4][C:3]1=[O:20].S(Cl)(Cl)=O.Cl>C1(C)C=CC=CC=1.CN(C=O)C>[CH3:19][C:8]1[CH:9]=[C:10]([C:11]([CH3:18])([CH3:17])[CH2:12][C:13]([CH3:15])([CH3:14])[CH3:16])[C:5]2[O:4][C:3](=[O:20])[C:2](=[C:2]3[C:6]4[CH:7]=[C:8]([CH3:19])[CH:9]=[C:10]([C:11]([CH3:18])([CH3:17])[CH2:12][C:13]([CH3:15])([CH3:14])[CH3:16])[C:5]=4[O:4][C:3]3=[O:20])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 18620260HCID 18620260, compound

Product 1

HCID 53759908HCID 53759908, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
373 K

Procedure

7.1 g of 3-hydroxy-5-methyl-7-(1,1,3,3-tetramethyl-butyl)-3H-benzofuran-2-one (U.S. Pat. No. 5,614,572, column 35, compound No 111) are placed in 12.5 ml of toluene, and 3 drops of DMF and 2.7 ml of thionyl chloride are added thereto. The solution is then slowly heated to 373 K at such a rate that the evolution of HCl and SO2 remains vigorous yet controllable. It is then stirred at 373 K for 1 hour. Approximately 12 ml of liquid are then distilled off in order to remove the excess thionyl chloride. The residue is diluted with 37.5 ml of toluene and, at room temperature, 3.5 ml of triethylamine are added dropwise. The thick, red reaction mixture is then heated to reflux temperature and boiled for 30 min. After cooling to room temperature, the triethylamine hydrochloride which has precipitated is filtered off, and the filtrate is concentrated to an oily consistency using a rotary evaporator. The isoxindigo is crystallised out by adding 25 ml of acetonitrile, is filtered off, washed with acetonitrile and dried, yielding 3.45 g (53% of the theoretical yield) of 5,5′-dimethyl-7,7′-bis(1,1,3,3-tetra-methyl-butyl)-[3,3′]bibenzofuranylidene-2,2′-dione of formula (LIIa).

Workup

  1. distillationApproximately 12 ml of liquid are then distilled off in order
  2. customto remove the excess thionyl chloride
  3. additionThe residue is diluted with 37.5 ml of toluene and, at room temperature
  4. addition3.5 ml of triethylamine are added dropwise
  5. temperatureThe thick, red reaction mixture is then heated
  6. temperatureto reflux temperature
  7. waitboiled for 30 min
  8. temperatureAfter cooling to room temperature
  9. customthe triethylamine hydrochloride which has precipitated
  10. filtrationis filtered off
  11. concentrationthe filtrate is concentrated to an oily consistency
  12. customa rotary evaporator
  13. customThe isoxindigo is crystallised out
  14. additionby adding 25 ml of acetonitrile
  15. filtrationis filtered off
  16. washwashed with acetonitrile
  17. customdried
  18. customyielding 3.45 g (53% of the

Sources & evidence

ORD record
ord-071609ac54774c9b8e0213c8ba4f29ff
Source dataset
uspto-grants-2001_08
Patent number
US06281361B1

Reaction notes

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