Lithium Bromide → HCID 12429026, compound

HRID 258582Notes

Reaction equation

HRID 258582 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2([CH3:28])[C:21]3[S:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18][C:17]=3[CH2:16][CH2:15][O:14]2)(=O)=O)=CC=1.[Br-:30].[Li+]>CC(C)=O>[Br:30][CH2:11][CH2:12][C:13]1([CH3:28])[C:21]2[S:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][C:17]=2[CH2:16][CH2:15][O:14]1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 12429025HCID 12429025, compound

Product 1

HCID 12429026HCID 12429026, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-[2-(p-toluenesulfonyloxy)ethyl]-6,7-dihydro-4-methyl-2-phenyl-4H-pyrano[4,3-d]thiazole (16 g, 37.2 mmoles, described above), and lithium bromide (16 g) in dry acetone (100 ml) is heated at reflux temperature for two hr. The solvent is removed under reduced pressure, water is added and the aqueous solution is extracted with ether. The ether solution is washed with water, dried over sodium sulfate, treated with charcoal and evaporated under reduced pressure to give 4-(2-bromoethyl)-6,7-dihydro-4-methyl-2-phenyl-4H-pyrano[4,3-d]thiazole, γmaxCHCl3 1545, 1500, 1465 and 1090 cm-1.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for two hr
  3. customThe solvent is removed under reduced pressure, water
  4. additionis added
  5. extractionthe aqueous solution is extracted with ether
  6. washThe ether solution is washed with water
  7. dry with materialdried over sodium sulfate
  8. additiontreated with charcoal
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0d5d7429c27c49249da33280245968a8
Source dataset
uspto-grants-1977_07
Patent number
US04033977

Reaction notes

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