Toluene → HCID 13251036, compound

HRID 1649355Notes

Reaction equation

HRID 1649355 reaction equation
[CH3:1][Si:2]([CH3:29])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5]C1C=C(S([O-])(=O)=O)C=CC=1C.[CH2:30]([O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1)[CH3:31].C1(C)C=CC=CC=1.CCCCCCC>ClCCl>[CH2:30]([O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37]([NH:40][CH2:5][CH2:4][CH2:3][Si:2]([CH3:29])([CH3:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:36][CH:35]=1)[CH3:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 2337Benzocaine2×HCID 8900HeptaneHCID 86739117HCID 86739117, compound

Product 1

HCID 13251036HCID 13251036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, 26.8 g of 4,4-dimethyl-4-sila-n-hexadecyl-p-toluenesulphonate, mixed with 35 g (in excess) of ethyl-p-aminobenzoate is heated at 123° to 128° for 4 hrs. The hot mixture is diluted with about 120 ml. of toluene and allowed to cool. The solution is then further diluted with dichloromethane. The resulting mixture is then washed with about 50 ml. of dilute aqueous sodium hydroxide, then washed with brine, and then dried over anh. sodium sulfate, filtered, and the filtrate concentrated by evaporating to obtain an oily residue. Heptane is added to the residue and upon standing two crops of solids (ethyl-p-aminobenzoate) are removed by filtering. The filtrate is concentrated to give an oily product which is placed on a chromatographic column, eluted with ethyl acetate/dichloromethane (5/95) to obtain several high quality fractions, which upon recrystallization from heptane, cooling to -20° gives refined title product, m.p. (39)--40°-41°. Additional crops of product are obtained from other fractions.

Workup

  1. temperatureis heated at 123° to 128° for 4 hrs
  2. additionThe hot mixture is diluted with about 120 ml
  3. temperatureto cool
  4. washThe resulting mixture is then washed with about 50 ml
  5. washof dilute aqueous sodium hydroxide, then washed with brine
  6. dry with materialdried over anh. sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customby evaporating
  10. customto obtain an oily residue
  11. customare removed
  12. filtrationby filtering
  13. concentrationThe filtrate is concentrated
  14. customto give an oily product which
  15. washeluted with ethyl acetate/dichloromethane (5/95)
  16. customto obtain several high quality fractions, which
  17. customupon recrystallization from heptane
  18. temperaturecooling to -20°

Sources & evidence

ORD record
ord-1b2329231915455f92c1a2624d77774c
Source dataset
uspto-grants-1983_11
Patent number
US04416876

Reaction notes

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