Toluene → HCID 13530898, compound

HRID 280268Notes

Reaction equation

HRID 280268 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=O.S(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.[CH2:32]([NH:35][CH2:36][CH2:37][CH3:38])[CH2:33][CH3:34]>O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([N:35]([CH2:36][CH2:37][CH3:38])[CH2:32][CH2:33][CH3:34])=[O:14]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8902DipropylamineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 135308972-(2-Methyl-3-nitrophenyl)acetic acid

Product 1

HCID 13530898HCID 13530898, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 22.0 g (0.105 mole) of 2-methyl-3-nitrophenylacetic acid and 25 cc of thionyl chloride was slowly heated to 75° and the copious evolution of gasses allowed to moderate. The temperature was raised and the solution was refluxed for 1 hour. The reaction was concentrated in vacuo. The residual straw-colored syrup was chased several times with dry toluene, diluted with 100 cc of dry toluene and added to a cool (10°) mixture of 13 g of sodium carbonate in 150 cc of water and 150 cc of toluene containing 14.5 cc (10.6 g, 0.12 mole) of di-n-propylamine with very slow stirring. After 30 minutes, the ice-bath was removed. Stirring was continued for one hour. An additional 0.5 g of solid sodium carbonate was added to the reaction. After 15 minutes, the organic phase was separated, washed with 5% aqueous sodium carbonate followed by 2N hydrochloric acid and, finally, water. The organic solution was dried over magnesium sulfate, concentrated in vacuo and pumped free of solvent to give 29.5 g of 2-methyl-3-nitrophenyl-N,N-di-n-propylacetamide as a straw-colored syrup.

Workup

  1. temperaturewas slowly heated to 75°
  2. temperatureThe temperature was raised
  3. temperaturethe solution was refluxed for 1 hour
  4. concentrationThe reaction was concentrated in vacuo
  5. additiondiluted with 100 cc of dry toluene
  6. additionadded to
  7. temperaturea cool
  8. customthe ice-bath was removed
  9. waitwas continued for one hour
  10. additionAn additional 0.5 g of solid sodium carbonate was added to the reaction
  11. waitAfter 15 minutes
  12. customthe organic phase was separated
  13. washwashed with 5% aqueous sodium carbonate
  14. dry with materialThe organic solution was dried over magnesium sulfate
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25f74a1071754ba6ac95766b03eaaa8d
Source dataset
uspto-grants-1986_05
Patent number
US04588740

Reaction notes

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