Triethylamine → 5,6-Dihydro-3-hydroxy-2-phenylthiazolo-[2,3-a]isoquinolinium hydroxide

HRID 477926Notes

Reaction equation

HRID 477926 reaction equation
[C:1]1(=[S:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.Br[CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](Cl)=[O:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH-:15].[OH:15][C:14]1[N+:2]2[CH2:3][CH2:4][C:5]3[C:10]([C:1]=2[S:11][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 598182Bromophenylacetyl chlorideHCID 28242121,2,3,4-Tetrahydroisoquinoline-1-thione

Product 1

HCID 190204015,6-Dihydro-3-hydroxy-2-phenylthiazolo-[2,3-a]isoquinolinium hydroxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(aa) Method A: 23.65 g of 3,4-dihydroisoquinoline-1(2H)-thione was dissolved in 750 ml of chloroform, whereupon the solution was treated at room temperature while cooling firstly with 54 g of α-bromophenylacetyl chloride and 90 minutes later with 53 ml of triethylamine and the mixture was stirred at room temperature overnight. The reaction mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. There was obtained 5,6-dihydro-3-hydroxy-2-phenylthiazolo[2,3-a]isoquinolinium hydroxide (internal salt) of m.p. 210° (dec.) (from acetonitrile/dioxane).

Workup

  1. additionwas treated at room temperature
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-35ff160048d04e2bb914d0341655b152
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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