Triethylamine → HCID 53819561, compound

HRID 1463841Notes

Reaction equation

HRID 1463841 reaction equation
[S:1]1[C:5]2[C:6]([C:10](Cl)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH:13]1[CH:14]=[CH:15][C:16](/[CH:19]=[CH:20]/[CH2:21][OH:22])=[CH:17][CH:18]=1.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[S:1]1[C:5]2[C:6]([C:10]([O:22][CH2:21][CH:20]=[CH:19][C:16]3[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=3)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5315892Cinnamyl AlcoholHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Product 1

HCID 53819561HCID 53819561, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 25 ml of dichloromethane are added dropwise at 15° C., with cooling and stirring, to a solution of 2.3 g of cinnamic alcohol, 3.5 g of triethylamine and a spatula tip of 4-dimethylaminopyridine in 13 ml of dichloromethane, the mixture is stirred for 16 hours at room temperature, ice-water is added, and the aqueous phase is extracted with dichloromethane. The extracts are washed with water, dried over Na2SO4 and concentrated by evaporation. The solid residue is triturated with a small amount of diethyl ether, yielding the title compound with a melting point of 70°-72° C.

Workup

  1. temperaturewith cooling
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. washThe extracts are washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation
  6. customThe solid residue is triturated with a small amount of diethyl ether

Sources & evidence

ORD record
ord-09b71fe41a0b485f8786ab6f98454ec5
Source dataset
uspto-grants-1994_04
Patent number
US05302607

Reaction notes

Loading…