Triethylamine → HCID 22162909, compound

HRID 1088429Notes

Reaction equation

HRID 1088429 reaction equation
[C:1]1([NH:11][C:12](=[O:17])[O:13][CH2:14][CH2:15][NH2:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)(Cl)Cl>[C:1]1([NH:11][C:12](=[O:17])[O:13][CH2:14][CH2:15][NH:16][S:28]([CH:27]=[CH2:26])(=[O:30])=[O:29])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 238716HCID 238716, compound

Product 1

HCID 22162909HCID 22162909, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-aminoethyl N-(1-naphthyl)carbamate [2.30 g(10.0 mmol.)] and triethylamine [1.53 ml(11.0 mmol.)] in chloroform(20 ml) was added, while stirring under ice-cooling, 2-chloroethanesulfonyl chloride [1.06 ml(10.0 mmol.)]. The mixture was stirred for 30 minutes under ice-cooling. The reaction mixture was washed with a 1N aqueous solution of sodium hydroxide, and dried, followed by distilling off the solvent under reduced pressure. The residue was subjected to a silica gel colum chromatography, eluting with hexane-ethyl acetate(1:1) to obtain the compound(270) [1.50 g(46.9%)] as a yellow oily product.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. washThe reaction mixture was washed with a 1N aqueous solution of sodium hydroxide
  5. customdried
  6. distillationby distilling off the solvent under reduced pressure
  7. washeluting with hexane-ethyl acetate(1:1)
  8. customto obtain the compound(270) [1.50 g(46.9%)] as a yellow oily product

Sources & evidence

ORD record
ord-0bcce5b44d3f415fbf09792b22c072af
Source dataset
uspto-grants-1990_10
Patent number
US04962113

Reaction notes

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