Sulfuryl chloride → HCID 20146207, compound

HRID 1248963Notes

Reaction equation

HRID 1248963 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]=1[OH:35])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(Cl)Cl.[CH2:39]([O:41][C:42]([C:44]1[CH:45]=[C:46]([N:50]2[C:54]([SH:55])=[N:53][N:52]=[N:51]2)[CH:47]=[CH:48][CH:49]=1)=[O:43])[CH3:40].S(Cl)(Cl)(=O)=O>ClCCl>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C:25]1[CH:34]=[C:33]([S:55][C:54]2[N:50]([C:46]3[CH:47]=[CH:48][CH:49]=[C:44]([C:42]([O:41][CH2:39][CH3:40])=[O:43])[CH:45]=3)[N:51]=[N:52][N:53]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]=1[OH:35])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 24648Sulfuryl chlorideHCID 25353Sulfur dichlorideHCID 1701642-Naphthalenecarboxamide, 1-hydroxy-N-[2-(tetradecyloxy)phenyl]-HCID 178468888HCID 178468888, compound

Product 1

HCID 20146207HCID 20146207, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

22.8 g of 2-(2-tetradecyloxyphenyl)carbamoyl-1-naphthol was dissolved in 100 ml of dichloromethane and to the solution was added dropwise at room temperature a dichloromethane solution of the sulfenyl chloride prepared from 25 g of 1-(3-ethoxycarbonylphenyl)-5-mercaptotetrazole and 13.5 g of sulfuryl chloride. After the completion of the addition, the mixture was stirred for 5 hours and the dichloromethane solution was washed with an aqueous solution of sodium hydrogencarbonate and then with water. The dichloromethane was distilled off under reduced pressure and the residue was crystallized from methanol to obtain 26.9 g of 2-(2-tetradecyloxyphenyl)carbamoyl-4-[1-(3-ethoxycarbonylphenyl)-5-tetrazolylthio]-1-naphthol. Yield: 74.3%. Melting Point: 88° to 90° C.

Workup

  1. additionAfter the completion of the addition
  2. washthe dichloromethane solution was washed with an aqueous solution of sodium hydrogencarbonate
  3. distillationThe dichloromethane was distilled off under reduced pressure
  4. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-08521387ce7a4c93bb1eb710cf3e4ccc
Source dataset
uspto-grants-1986_12
Patent number
US04628024

Reaction notes

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