Benzo(d)thiazol-2-amine → HCID 708625, compound

HRID 2085361Notes

Reaction equation

HRID 2085361 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][O:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:11][O:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)=[O:16]

Participants

6

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 708625HCID 708625, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The present example sets forth a method whereby the benzthiozole compounds may be obtained. However, other methods may be used in the practice of the present invention. A solution of 4.5 g of 2-aminobenzthiazole in 40 mL of dichloromethane and 10 mL of pyridine was cooled in an ice bath. To this cooled solution was slowly added a solution of 2-methoxybenzoyl chloride in 10 mL of dichloromethane. The resulting mixture was stirred for 3 hours while the ice bath slowly warmed to room temperature. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with 1 N HCl (2×50 mL), saturated NaHCO3 (1×40 mL), and saturated NaCl (1×50 mL). After drying over Na2SO4, the solution containing the crude product was filtered and evaporated to dryness. The resulting 8.0 g of white solid was recrystalized from ethyl acetate to afford 4.0 g of 2-(2 methoxybenzoylamino)benzthiazole as white crystals, mp 196-197° C., as first crop.

Workup

  1. custommay be obtained
  2. washwashed with 1 N HCl (2×50 mL), saturated NaHCO3 (1×40 mL), and saturated NaCl (1×50 mL)
  3. dry with materialAfter drying over Na2SO4
  4. additionthe solution containing the crude product
  5. filtrationwas filtered
  6. customevaporated to dryness
  7. customThe resulting 8.0 g of white solid was recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-b431c54b2bcb4a13a6b59b3dd8e274eb
Source dataset
uspto-grants-2004_04
Patent number
US06720344B2

Reaction notes

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