Toluene → HCID 19783412, compound

HRID 257514Notes

Reaction equation

HRID 257514 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([NH-:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.C1(C)C=CC=CC=1.O=S(Cl)Cl.[OH-].[K+]>O.CCOC(C)=O.CCCCCCC>[C:10]([C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)#[N:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 178514228HCID 178514228, compound

Product 1

HCID 19783412HCID 19783412, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of (2) (10 g, 61.28 mmol) i dry toluene (50 ml) was added SOCl2 (12 ml, 164.92 mmol) under N2. The reaction mixture was heated to 70° C. for 1 h. and then to 90° C. until TLC (AcOEt/Heptane 1:1) indicated complete reaction Water (20 ml) was slowly added to the ice cooled reaction mixture followed by 50% KOH until pH≈8. The organic layer was separated, and the aqueous layer was extracted with toluene (3×50 ml). The combined organic layers were washed with water (2×30 ml), brine (1×30 ml), dried (Na2SO4), and evaporated in vacuo to yield (3) as a solid (8.81 g, 99%). Recrystallization from abs. EtOH gave (3) as a white solid.

Workup

  1. customto 90° C.
  2. temperaturecooled
  3. customreaction mixture
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with toluene (3×50 ml)
  6. washThe combined organic layers were washed with water (2×30 ml), brine (1×30 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8129a9c059b946bbb77dae9c73b54c5c
Source dataset
uspto-grants-1993_11
Patent number
US05262430

Reaction notes

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