Hydrochloric Acid → HCID 53759908, compound

HRID 430726Notes

Reaction equation

HRID 430726 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>CN(C=O)C.C1(C)C=CC=CC=1>[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, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

7.1 g of 3-hydroxy-5-methyl-7-(1,1,3,3-tetramethylbutyl)-3H-benzofuran-2-one (U.S. Pat. No. 5,614,572, Column 35, Compound No. 111) are introduced into 12.5 ml of toluene as initial charge and admixed with 3 drops of DMF and 2.7 ml of thionyl chloride. The solution is then gradually heated to 100° C. so that the evolution of HCl and SO2 remains lively but still controllable. Thereafter the reaction mixture is stirred at 100° C. for a further 1 h. About 12 ml of liquid are subsequently distilled off to remove excess thionyl chloride. The residue is diluted with 37.5 ml of toluene and admixed at room temperature with 3.5 ml of triethylamine added dropwise. The thick red reaction mixture is then refluxed for 30 min. The precipitated triethylamine hydrochloride is filtered off after cooling to room temperature and the filtrate is concentrated in a rotary evaporator to an oily consistency. The isoxindigo is crystallized out by addition of 25 ml of acetonitrile, filtered off, washed with acetonitrile and dried to leave 3.45 g (53% of theory) of 5,5′-dimethyl-7,7′-bis(1,1,3,3-tetramethylbutyl)[3,3′]bibenzofuranylidene-2,2′-dione of the formula

Workup

  1. distillationAbout 12 ml of liquid are subsequently distilled off
  2. customto remove excess thionyl chloride
  3. additionThe residue is diluted with 37.5 ml of toluene
  4. customadmixed at room temperature with 3.5 ml of triethylamine
  5. additionadded dropwise
  6. customThe thick red reaction mixture
  7. temperatureis then refluxed for 30 min
  8. filtrationThe precipitated triethylamine hydrochloride is filtered off
  9. temperatureafter cooling to room temperature
  10. concentrationthe filtrate is concentrated in a rotary evaporator to an oily consistency
  11. customThe isoxindigo is crystallized out by addition of 25 ml of acetonitrile
  12. filtrationfiltered off
  13. washwashed with acetonitrile
  14. customdried

Sources & evidence

ORD record
ord-51aa76e00fc744a0ae203e027279d5f7
Source dataset
uspto-grants-2001_11
Patent number
US06323267B1

Reaction notes

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