Water → 5-chloro-3-[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl]-3H-benzothiazol-2-one

HRID 330807Notes

Reaction equation

HRID 330807 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.Br[CH2:13][C:14]1[CH:15]=[C:16]([C:20]2[N:24]=[C:23]([CH3:25])[O:22][N:21]=2)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[N:24]=[C:23]([CH3:25])[O:22][N:21]=4)[CH:15]=3)[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6038292(3H)-Benzothiazolone, 5-chloro-HCID 70605483-(3-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole

Product 1

HCID 468467275-chloro-3-[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl]-3H-benzothiazol-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 100 mg (0.54 mmol) of 5-chloro-3H-benzothiazol-2-one, 153 mg (0.59 mmol) of 3-(3-bromomethylphenyl)-5-methyl-1,2,4-oxadiazole and 303 mg (2.16 mmol) of potassium carbonate in 20 ml of acetonitrile are stirred at 80° C. for 1 h. 30 ml of water are added to the reaction mixture, which is then extracted with MTBE, dried and evaporated to dryness. The crude product is purified by column chromatography on silica gel and stirred with ether, giving “A12”: ESI: 358 (M+H); Rt.=3.25 min (method A);

Workup

  1. extractionis then extracted with MTBE
  2. customdried
  3. customevaporated to dryness
  4. customThe crude product is purified by column chromatography on silica gel
  5. stirringstirred with ether
  6. customgiving “A12”
  7. custom=3.25 min (method A)

Sources & evidence

ORD record
ord-f09265ae30754b2eadccc6f75fc240fa
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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