Sodium Azide → HCID 20482496, compound

HRID 1389665Notes

Reaction equation

HRID 1389665 reaction equation
CS(O[CH:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+].N(C(CCCCCCCCCC)CCCCCNC1C=CC(C(O)=O)=CC=1)=[N+]=[N-]>CN(C)C=O>[N:34]([CH:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1)=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 20482478HCID 20482478, compoundHCID 20482499HCID 20482499, compound

Product 1

HCID 20482496HCID 20482496, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.4 g. of ethyl 4-(6-methanesulfonyloxyhexadecylamino)benzoate and 1.9 g. of sodium azide in 65 ml. of dimethylformamide is stirred at ambient temperature for 16 hours, poured into 200 ml. of water, and extracted with chloroform. The organic extract is washed with saturated sodium chloride solution, dried over sodium sulfate, and evaporated. Crystallization of the residue from hexane yields the product. The ester is hydrolyzed to 4-(6-azidohexadecylamino)benzoic acid using the procedure of Example 10.

Workup

  1. additionpoured into 200 ml
  2. extractionof water, and extracted with chloroform
  3. extractionThe organic extract
  4. washis washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customCrystallization of the residue from hexane
  8. customyields the product

Sources & evidence

ORD record
ord-a43cf6599c7a4a4aa484eee0f0624b99
Source dataset
uspto-grants-1981_01
Patent number
US04245097

Reaction notes

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