HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → N,N-Dioctadecyl-3-(6-hydroxy-1-naphthylsulfamoyl)benzamide

HRID 647232
Notes
Print preview

Reaction equation

HRID 647232 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([OH:12])=[CH:7]2.S(Cl)(Cl)(=O)=O.[CH2:18]([N:36]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[C:37](=[O:48])[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([S:44](Cl)(=[O:46])=[O:45])[CH:39]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].Cl>N1C=CC=CC=1>[CH2:49]([N:36]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:37](=[O:48])[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([S:44](=[O:45])(=[O:46])[NH:1][C:2]2[C:3]3[C:8](=[CH:7][C:6]([OH:12])=[CH:5][CH:4]=3)[CH:9]=[CH:10][CH:11]=2)[CH:39]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68655-Amino-2-naphtholHCID 24648Sulfuryl chlorideHCID 204858833-(Dioctadecylcarbamoyl)benzene-1-sulfonyl chloride

Product 1

HCID 20485877N,N-Dioctadecyl-3-(6-hydroxy-1-naphthylsulfamoyl)benzamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-amino-2-naphthol (8.0 g, 0.05 mol) in pyridine (80 ml) was added the sulfonyl chloride, N,N-dioctadecyl-3-chlorosulfonylbenzamide (Example 5) (36.2 g, 0.05 mol). The reaction was stirred overnight at room temperature and then poured into excess dilute hydrochloric acid. The mixture was extracted with dichloromethane, washed with water, dried over magnesium sulfate and suction-filtered through a pad of decolorizing carbon. The filtrate was concentrated to an oil which was crystallized from acetonitrile to yield 26.5 g of product.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationsuction-filtered through a pad of decolorizing carbon
  5. concentrationThe filtrate was concentrated to an oil which
  6. customwas crystallized from acetonitrile

Sources & evidence

ORD record
ord-34001c52fb1846848e1759637e8c9b9e
Source dataset
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04407930

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes