Dichloromethane → 2-Phenyl-5,6,7,8-tetrahydrothiazolo[2,3-b]-benzothiazol-3(2H)-one

HRID 1680636Notes

Reaction equation

HRID 1680636 reaction equation
[Br-].[OH:2][C:3]1[N+:10]2[C:9]3[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=3[S:7][C:6]=2[S:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)Cl>O>[C:15]1([CH:4]2[S:5][CH:6]3[S:7][C:8]4[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=4[N:10]3[C:3]2=[O:2])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 129123733-Hydroxy-2-phenyl-5,6,7,8-tetrahydrothiazolo[2,3-b]benzothiazolium bromide

Product 1

HCID 234553242-Phenyl-5,6,7,8-tetrahydrothiazolo[2,3-b]-benzothiazol-3(2H)-oneYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.7 g. (0.026 moles) of 3-hydroxy-2-phenyl-5,6,7,8-tetrahydrothiazolo[2,3-b]benzothiazolium bromide, prepared according to Example 10, is suspended in a mixture of 1000 ml. methylene chloride and 500 ml. water, and the mixture is stirred at room temperature for 5 hours. The layers are separated and the methylene chloride layer is dried over anhydrous magnesium sulfate. The drying agent is removed by filtration and the filtrate is reduced in volume. The residual solid is triturated with ether and the yellow solid is collected. The crude material is recrystallized from 1.5 l. of acetonitrile to yield a yellow solid weighing 4.7 g. (63% yield). The product melts at ca. 200° C.(dec.).

Workup

  1. additionis suspended in a mixture of 1000 ml
  2. customThe layers are separated
  3. dry with materialthe methylene chloride layer is dried over anhydrous magnesium sulfate
  4. customThe drying agent is removed by filtration
  5. customThe residual solid is triturated with ether
  6. customthe yellow solid is collected
  7. customThe crude material is recrystallized from 1.5 l
  8. customof acetonitrile to yield a yellow solid

Sources & evidence

ORD record
ord-362daa81e0604f8880967716687a987d
Source dataset
uspto-grants-1981_06
Patent number
US04275065

Reaction notes

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