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

HRID 1087540Notes

Reaction equation

HRID 1087540 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. additionwhereupon the solution was 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-577b825c7e0f4082a869ec9b130e13af
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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