2-Chloro-6-methylaniline → Tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-YL)carbamate

HRID 2201970Notes

Reaction equation

HRID 2201970 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[S:18][C:19]([C:22](Cl)=[O:23])=[CH:20][N:21]=1)([CH3:13])([CH3:12])[CH3:11].C(NC(C)C)(C)C>ClCCl>[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[S:18][C:19]([C:22](=[O:23])[NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[Cl:1])=[CH:20][N:21]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 68972-Chloro-6-methylanilineHCID 7912DiisopropylamineHCID 45117870tert-Butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate

Product 1

HCID 18184791Tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-YL)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The fourth step involves adding 2-chloro-6-methylaniline to a stirred solution of tert-butyl[5-(chlorocarbonyl)-1,3-thiazol-2-yl]carbamate in dichloromethane at 0° C. Diisopropylamine was added to the reaction mixture, warmed to room temperature, stirred for 24 hours, diluted with dichloromethane, and washed with 2N hydrochloric acid. The organic extract thus obtained was dried, filtered, and concentrated to obtain a residue. The residue was diluted with ethyl acetate-ether, filtered, washed with ether, and dried in vacuo to obtain tert-butyl{5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazol-2-yl}carbamate (Formula 1b) in an overall yield of 48%.

Workup

  1. washwashed with 2N hydrochloric acid
  2. extractionThe organic extract thus
  3. customobtained
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a residue
  8. filtrationfiltered
  9. washwashed with ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-47d4c880a60542dd8f71c89302ffef91
Source dataset
uspto-grants-2016_06
Patent number
US09365526B2

Reaction notes

Loading…