Hydrochloric Acid → HCID 20485877, compound

HRID 647232Notes

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]

Participants

6

Reactant 4

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

Product 1

HCID 20485877HCID 20485877, compoundYield 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
Patent number
US04407930

Reaction notes

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