2-Chlorobenzothiazole → HCID 11189033, compound

HRID 1593523Notes

Reaction equation

HRID 1593523 reaction equation
Cl[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:14]=[C:15]([CH:17]=[CH:18][C:19]=1[CH3:20])[NH2:16].[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C(O)(=O)C>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:16]([C:15]1[CH:17]=[CH:18][C:19]([CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=1)[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=1[Cl:21]

Participants

5

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 278823-Methoxy-4-methylanilineHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 11189033HCID 11189033, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 0.339 g (2 mmol) 2-Chlorobenzthiazole (commercially available) and 0.275 g (2 mmol) 3-methoxy-4-methylaniline (commercially available) in 4 ml acetic acid was heated to 115° C. for 4 h. After cooling to room temperature the mixture was subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. The product fractions of Benzothiazol-2-yl-(3-methoxy-4-methyl-phenyl)-amine were evaporated to dryness and reacted according to the procedure described for Example 2 with 2-chlorobenzoyl chloride to yield the title compound. MS (m/e): 409.3 (MH+, 100%). According to the procedure described for Example 35 further N-Benzothiazol-2-yl-N-(aryl)-benzamide derivatives have been synthesised by reaction of 2-chlorobenzthiazole with the respective aniline (commercially available) and subsequently with the respective acid chloride. The results are shown in table 2 below and comprise Example 36 to Example 43.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customHPLC separation on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customThe product fractions of Benzothiazol-2-yl-(3-methoxy-4-methyl-phenyl)-amine were evaporated to dryness
  5. customreacted

Sources & evidence

ORD record
ord-9e7fd1bb5c9b4dafbd30bd06624f2b85
Source dataset
uspto-grants-2007_11
Patent number
US07297707B2

Reaction notes

Loading…