Acetic Acid → 2-Amino-5-bromobenzene-1-thiol

HRID 2103659Notes

Reaction equation

HRID 2103659 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6]C(=O)[S:8][C:4]=2[CH:3]=1.[OH-].[Na+].C(O)(=O)C>O>[NH2:6][C:5]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=1[SH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 1884446-Bromo-2,3-dihydro-1,3-benzothiazol-2-one

Product 1

HCID 12090452-Amino-5-bromobenzene-1-thiolYield 112.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Bromo-2-benzothiazolinone (4.65 g, 20.0 mmole) and sodium hydroxide (15.4 g, 0.385 mole) were mixed in 40 ml water. The mixture was stirred at room temperature for 30 minutes to form a slurry, was then heated at 100° C. and became a clear solution. The mixture continued to stir at 100° C. overnight after which it was cooled to room temperature. While cooling in an ice bath, the pH of the solution was adjusted to 6 with acetic acid (22 ml). The resulting solid was collected by filtration, washed three times (3×) with water and dried under vacuum to give 4.60 g of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.23 (s, 1H), 6.98 (d, J=7.80 Hz, 1H), 6.59 (d, J=8.82 Hz, 1H), 5.41 (br, 2H). MS: (M+H)+=203/205, (M+H)+=406.

Workup

  1. customto form a slurry
  2. temperaturewas then heated at 100° C.
  3. stirringto stir at 100° C. overnight after which it
  4. temperaturewas cooled to room temperature
  5. temperatureWhile cooling in an ice bath
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed three times (3×) with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-fed1e02c010c4434a754466d368cce77
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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