Hydrochloric Acid → HCID 18413842, compound

HRID 991412Notes

Reaction equation

HRID 991412 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[C:8]([Cl:13])=[CH:7][C:5]=2[N:6]=1.[OH-].[K+].BrC[C:18]([CH2:26][CH3:27])([CH2:22][CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20].Cl>O>[NH2:6][C:5]1[CH:7]=[C:8]([Cl:13])[C:9]([O:11][CH3:12])=[CH:10][C:4]=1[S:3][CH2:2][C:18]([CH2:26][CH3:27])([CH2:22][CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 9453545-chloro-6-methoxy-1,3-benzothiazol-2-amineHCID 10466667HCID 10466667, compound

Product 1

HCID 18413842HCID 18413842, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4 (20.0 g) in H2O (200 ml) was added KOH (100 g). The slurry was refluxed for 7 h and allowed to cool to RT. To the dark solution was added 2 (33.2 g) in one portion. The reaction mixture was stirred for 18 h at which point the pH was adjusted to 4 with HCl. The mixture was transferred to a separatory funnel and extracted three times with ethyl acetate. The organic layer was dried and concentrated. The product was purified by column chromatography on silica gel eluting the product with 10% ethyl acetate/petroleum ether giving 5 (30.1 g).

Workup

  1. temperatureThe slurry was refluxed for 7 h
  2. customThe mixture was transferred to a separatory funnel
  3. extractionextracted three times with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography on silica gel eluting the product with 10% ethyl acetate/petroleum ether giving 5 (30.1 g)

Sources & evidence

ORD record
ord-d973a457b6494975afb758658321d16a
Source dataset
uspto-grants-2002_10
Patent number
US06465451B1

Reaction notes

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