Trifluoroacetic acid → 2-Bromo-4,5,6,7-tetrahydro-1,3-benzothiazol-6-amine

HRID 1402675Notes

Reaction equation

HRID 1402675 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:17][CH2:16][C:11]2[N:12]=[C:13]([Br:15])[S:14][C:10]=2[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:15][C:13]1[S:14][C:10]2[CH2:9][CH:8]([NH2:7])[CH2:17][CH2:16][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71748507tert-Butyl (2-bromo-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)carbamate

Product 1

HCID 666106712-Bromo-4,5,6,7-tetrahydro-1,3-benzothiazol-6-amineYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-Bromo-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester (0.50 grams, 1.5 mmol, obtained in preparation 2) in dichloromethane (30 mL) was treated with trifluroacetic acid (1.1 mL, 15 mmol) at 0° C. Reaction mass was stirred for 4 hours. After completion of the reaction, the mass was quenched with ice cold water and adjusted pH to 10, by using 40% aqueous sodium hydroxide solution. The product was extracted with dichloromethane (3×50 mL) and the combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. The organic volatiles were evaporated under vacuum to obtain the title compound (0.36 grams).

Workup

  1. customReaction mass
  2. customAfter completion of the reaction
  3. customthe mass was quenched with ice cold water and adjusted pH to 10
  4. extractionThe product was extracted with dichloromethane (3×50 mL)
  5. washthe combined organics were washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe organic volatiles were evaporated under vacuum

Sources & evidence

ORD record
ord-2eea4cff53f34eb1a5b259a9461a936e
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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