Sodium Hydroxide → 2H-[1,3]Dioxolo[4,5-f][1,3]benzothiazol-6-amine

HRID 2399722Notes

Reaction equation

HRID 2399722 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11]([NH2:13])=[S:12])=[CH:4][C:3]=2[O:2]1.BrBr.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[NH2:13][C:11]1[S:12][C:6]2[CH:7]=[C:8]3[O:9][CH2:1][O:2][C:3]3=[CH:4][C:5]=2[N:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 1471599N-2H-1,3-Benzodioxol-5-ylthiourea

Product 1

HCID 20499002H-[1,3]Dioxolo[4,5-f][1,3]benzothiazol-6-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

3,4-Methylenedioxyphenylthiourea (1.96 g; Lancaster Chemical Co) in chloroform (6 cm3) was stirred at ambient temperature and a solution of bromine (0.37 cm3) in chloroform (3 cm3) was added in portions. The mixture was cooled using a water bath and after 1 hr. was stored for 64 hr., diluted with water (100 cm3), basified with aqueous 2M sodium hydroxide and extracted with ethyl acetate (2×150 cm3). The combined organic phases were washed with water and dried (magnesium sulphate). The solution was evaporated under reduced pressure to give the required product as a pale pink solid; mp 200° C.; 1H NMR (CDCl3): δ7.06 (1H,s); 7.02(1H,s); 5.98(2H,s); 5.0(broad signal, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. waitwas stored for 64 hr
  3. extractionextracted with ethyl acetate (2×150 cm3)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (magnesium sulphate)
  6. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3186fd65967446b2b3b858abda5184bd
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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