Sulfuryl chloride → HCID 20146207, compound

HRID 569717Notes

Reaction equation

HRID 569717 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 6344DichloromethaneSolvent3×

Procedure

2-(2-Tetradecyloxyphenyl)carbamoyl-1-naphthol (22.8 g) was dissolved in 100 ml of dichloromethane, and a dichloromethane solution of sulphenyl chloride prepared from 25 g of 1-(3-ethoxycarbonylphenyl)-5-mercaptotetrazole and 13.5 g of sulfuryl chloride was added dropwise thereto at room temperature. The resulting dichloromethane solution was stirred for an additional 5 hours, and washed with an aqueous sodium bicarbonate solution and further with water. The dichloromethane was distilled away 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, m.p., 88°-90° C. Yield was 74.3%.

Workup

  1. additionwas added dropwise
  2. customat room temperature
  3. washwashed with an aqueous sodium bicarbonate solution and further with water
  4. distillationThe dichloromethane was distilled away under reduced pressure
  5. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-f30d03954bd44bd9bda07b5597a8dab2
Source dataset
uspto-grants-1988_03
Patent number
US04734357

Reaction notes

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