Acetone → 1-Benzoyloxy-4-(3-bromoacetylbenzenesulfonamido)-N,N-dioctadecyl-2-naphthamide

HRID 851529Notes

Reaction equation

HRID 851529 reaction equation
[C:1]([O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:32])[CH3:31])[CH:25]=2)(=[O:23])=[O:22])=[CH:12][C:11]=1[C:33]([N:35]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[O:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:72]Br.CC(C)=O>O1CCOCC1.CCCCCC>[C:1]([O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:32])[CH2:31][Br:72])[CH:25]=2)(=[O:23])=[O:22])=[CH:12][C:11]=1[C:33]([N:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])=[O:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 24408Bromine2×HCID 204932281-benzoyloxy-4-(3-acetylbenzenesulfonamido)-N,N-dioctadecyl-2-naphthamide

Product 1

HCID 541027471-Benzoyloxy-4-(3-bromoacetylbenzenesulfonamido)-N,N-dioctadecyl-2-naphthamideYield 89.1%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 15.7 g (15.7 mmol) of 1-benzoyloxy-4-(3-acetylbenzenesulfonamido)-N,N-dioctadecyl-2-naphthamide in 150 ml of dioxane was treated with 2.51 g (15.7 mmoles) of bromine at 40° to 45° C. The reaction was held for one hour at this temperature, during which time the bromine color discharged. Analysis by TLC (25 percent acetone in hexane) indicated a complete reaction and only one main product was observed. The solution was drowned to ice water and the resulting mixture was extracted with chloroform. The chloroform extracts were combined and washed well with water, dried (MgSO4), and stripped to give 15 g (89 percent) of an oil which was used without further purification.

Workup

  1. customa complete reaction and only one main product
  2. extractionthe resulting mixture was extracted with chloroform
  3. washwashed well with water
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-b8f81e2ff54a478bba08d03c09cbc905
Source dataset
uspto-grants-1983_05
Patent number
US04385104

Reaction notes

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