Acetone → 3-Hydroxy-2-phenyl-5,6,7,8-tetrahydrothiazolo[2,3-b]benzothiazolium bromide

HRID 1680635Notes

Reaction equation

HRID 1680635 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[Br:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](O)=[O:14].CC(C)=O.C(OC(=O)C)(=O)C>C(O)(=O)C>[Br-:11].[OH:14][C:13]1[N+:6]2[C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[S:3][C:2]=2[S:1][C:12]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7918Acetic AnhydrideHCID 97919Bromo(phenyl)acetic acidHCID 1785278174,5,6,7-Tetrahydro-1,3-benzothiazole-2-thiol

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9.0 g. (0.053 moles) 2-mercapto-4,5,6,7-tetrahydrobenzothiazole and 10.75 g. (0.053 moles) α-bromophenylacetic acid are dissolved in 500 ml. of acetone, to which is further added 50 ml. each of glacial acetic acid and acetic anhydride. The mixture is heated in an open flask and the volume reduced to 100 ml. The precipitated solid is collected. The solid weighs 13 g. (67%) and melts at 233°-235° C.(dec.).

Workup

  1. temperatureThe mixture is heated in an open flask
  2. customThe precipitated solid is collected

Sources & evidence

ORD record
ord-1c603506de7f472c82f5613359a60733
Source dataset
uspto-grants-1981_06
Patent number
US04275065

Reaction notes

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