Thionyl Chloride → HCID 21163356, compound

HRID 904262Notes

Reaction equation

HRID 904262 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)([O:10][CH3:11])=[O:9].S(Cl)(Cl)=O>C(COC)OC.C(Cl)Cl.CC(N(C)C)=O.O>[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:33])=[CH:30][CH:29]=1)([O:10][CH3:11])=[O:9]

Participants

9

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acid

Product 1

HCID 21163356HCID 21163356, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 19.0 g. of methanesulfonamide in 150 ml. of dry dimethylacetamide is added dropwise during 15 minutes to a stirred and cooled (water bath) suspension of 5.5 g. of sodium hydride in 100 ml. of dry dimethylacetamide. The mixture is then stirred and heated at 60°-80° C. for 2 hours. In the meantime, a mixture of 36.2 g. of p-(15-carbomethoxypentadecylamino)benzoic acid in 1200 ml. of methylene chloride, 300 ml. of dimethoxyethane and 40 ml. of thionyl chloride is refluxed for 1 hour and 15 minutes. The solution is evaporated to an oil which is coevaporated twice with added dioxane to remove excess thionyl chloride. To the resulting oily residue p-(15-carbomethoxypentadecylamino)benzoyl chloride hydrochloride is added, in one portion, the previously prepared mixture of sodium methanesulfonamide in dimethylacetamide. The mixture becomes very hot and is cooled briefly in a water bath and then is stirred at room temperature for 30 minutes. The mixture is filtered through a bed of diatomaceous earth and the filtrate is poured into 2 l. of water. The resulting suspension is coagulated by the addition of 250 ml. of saturated sodium chloride solution and the mixture is filtered. The product is washed with water, partially air dried and then crystallized from 1.5 l. of ethanol. The product is recrystallized from p-dioxane and dried at 65° C. to yield the title compound as tan crystals.

Workup

  1. temperaturecooled
  2. stirringThe mixture is then stirred
  3. temperatureheated at 60°-80° C. for 2 hours
  4. additionIn the meantime, a mixture of 36.2 g
  5. customThe solution is evaporated to an oil which
  6. customto remove excess thionyl chloride
  7. additionTo the resulting oily residue p-(15-carbomethoxypentadecylamino)benzoyl chloride hydrochloride is added, in one portion
  8. additionthe previously prepared mixture of sodium methanesulfonamide in dimethylacetamide
  9. temperatureis cooled briefly in a water bath
  10. stirringis stirred at room temperature for 30 minutes
  11. filtrationThe mixture is filtered through a bed of diatomaceous earth
  12. additionthe filtrate is poured into 2 l
  13. additionThe resulting suspension is coagulated by the addition of 250 ml
  14. filtrationof saturated sodium chloride solution and the mixture is filtered
  15. washThe product is washed with water, partially air
  16. customdried
  17. customcrystallized from 1.5 l
  18. customThe product is recrystallized from p-dioxane
  19. customdried at 65° C.

Sources & evidence

ORD record
ord-e2e0abdb64c54a28b0a156a05459190d
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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