Hydrochloric Acid → 2-Amino-4,7-dihydro-1,3-benzothiazol-6(5H)-one

HRID 1835613Notes

Reaction equation

HRID 1835613 reaction equation
Br.[NH2:2][C:3]1[S:4][C:5]2[CH2:11][C:10](OC)([O:12]C)[CH2:9][CH2:8][C:6]=2[N:7]=1.Cl.[OH-].[Na+]>O>[NH2:2][C:3]1[S:4][C:5]2[CH2:11][C:10](=[O:12])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 235040542-amino-6,6-dimethoxy-4,5,6,7-tetrahydrobenzothiazole Hydrobromide

Product 1

HCID 98774852-Amino-4,7-dihydro-1,3-benzothiazol-6(5H)-oneYield 87.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

21.9 g of the dimethoxy compound from example 2 was suspended in 205 ml of water and heated to 45° C. for dissolution. Then 7.3 ml of concentrated HCl was added and the solution was stirred at 60° C. for 30 minutes. Reaction mixture was cooled to ambient temperature and neutralised with 40% aqueous NaOH. Precipitated solid was filtered off, washed with water and dried to yield 10.9 g of the title product. For analytical purposes, the sample of the product was recrystalized from hot isopropanol.

Workup

  1. customReaction mixture
  2. customPrecipitated solid
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7af156a5bca940748de1ad4bccf5acf9
Source dataset
uspto-grants-2004_08
Patent number
US06770761B2

Reaction notes

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