Bromine → 4-Fluoro-7-methoxy-1,3-benzothiazol-2-amine

HRID 2178661Notes

Reaction equation

HRID 2178661 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]([NH2:13])=[S:12].BrBr.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]2[N:10]=[C:11]([NH2:13])[S:12][C:4]=2[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 80212359HCID 80212359, compound

Product 1

HCID 717431044-Fluoro-7-methoxy-1,3-benzothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 1-(2-fluoro-5-methoxyphenyl)thiourea (C11) (17.30 g, 86.40 mmol) in chloroform (160 mL) at 0° C. was added bromine (4.44 mL, 86.4 mmol) drop-wise. The reaction mixture was stirred at room temperature for 30 minutes and was then heated to reflux for 18 hours. It was poured into ice water (1.0 L) containing an excess of sodium bicarbonate. The resulting precipitate was collected by filtration and washed with water and hexanes to afford the title compound as a white solid. Yield: 15.40 g, 77.69 mmol, 90%. 1H NMR (300 MHz, DMSO-d6): δ 3.84 (s, 3H), 6.60 (m, 1H), 7.03 (m, 1H), 7.73 (s, 2H),

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 18 hours
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water and hexanes

Sources & evidence

ORD record
ord-ace935cb16c04e2bbf16f25d48f788ba
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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