Carbon Dioxide → 1,3-Benzothiazole-2-carboxylic acid

HRID 982024

Reaction equation

HRID 982024 reaction equation
C([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[C:15](=[O:17])=[O:16].O>O1CCCC1>[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 7222BenzothiazoleHCID 178418339Butyllithium

Product 1

HCID 5850531,3-Benzothiazole-2-carboxylic acidYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A precooled (-78° C.) solution of 7.7 ml (19.2 mmol) of n-butyllithium in 50 ml of dry tetrahydrofuran was treated dropwise with 2.0 ml (18.3 mmol) of benzothiazole. After the addition was complete, the solution was poured into a mixture of excess dry ice in 100 ml of tetrahydrofuran. After being allowed to warm, the resulting solution was treated with water, washed with ether, acidified with HCl, and filtered to give a yellow solid. Digestion with boiling ether followed by filtration gave 1.55 g (47%) of the desired compound as a nearly white solid.

Workup

  1. additionAfter the addition
  2. temperatureto warm
  3. washwashed with ether
  4. filtrationfiltered
  5. customto give a yellow solid
  6. filtrationDigestion with boiling ether followed by filtration

Sources & evidence

ORD record
ord-defdc355577a4f3f883df978a3b7f93a
Source dataset
uspto-grants-1991_02
Patent number
US04994477

Linked notes

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