Chloride → HCID 54048902, compound

HRID 904493Notes

Reaction equation

HRID 904493 reaction equation
[CH2:1]([NH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15].[C:26](=[O:29])([O-])[O-:27].[Na+].[Na+].[Cl-:32].S(Cl)(Cl)=O>C1(C)C=CC=CC=1.O.C(Cl)(Cl)Cl>[C:26]([N:16]([CH2:1][CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])[C:17]1[CH:18]=[CH:19][C:20]([C:21]([Cl:32])=[O:23])=[CH:24][CH:25]=1)([O:27][CH2:21][C:20]1[CH:24]=[CH:25][CH:17]=[CH:18][CH:19]=1)=[O:29]

Participants

8

Reactant 4

HCID 312ChlorideHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 54054435HCID 54054435, compound

Product 1

HCID 54048902HCID 54048902, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. of 4-(4,14-pentadecadienylamino)benzoic acid in 200 mml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred mixture is added 10 g. carbobenzoyl chloride. After 2 hours stirring at 40° C., the layers are separated, the chloroform layer is washed three times with 1N hydrochloric acid, dried, and the solvent evaporated to yield an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. of thionyl chloride, and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.

Workup

  1. additionTo the vigorously stirred mixture is added 10 g
  2. customthe layers are separated
  3. washthe chloroform layer is washed three times with 1N hydrochloric acid
  4. customdried
  5. customthe solvent evaporated
  6. customto yield an oil
  7. dissolutionThe oil is dissolved in 300 ml
  8. customThe solvents are evaporated
  9. dissolutionthe residue is dissolved three times in toluene
  10. customevaporating each time
  11. customto yield a viscous, orange oil

Sources & evidence

ORD record
ord-a7be4f8dcf3748b18fa89c2bc234da93
Source dataset
uspto-grants-1980_10
Patent number
US04230878

Reaction notes

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