Phosgene → HCID 66661769, compound

HRID 1882369Notes

Reaction equation

HRID 1882369 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[S:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=1.[C:20](Cl)(Cl)=[O:21].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:14][C:12]1[N:13]=[C:9]([N:8]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:20]2=[O:21])[S:10][C:11]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 86635197HCID 86635197, compound

Product 1

HCID 66661769HCID 66661769, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of ethyl 2-(2-aminophenylamino)-4-methylthiazole-5-carboxylate (0.24 g, 0.87 mmol) in dichloromethane (12 mL) was added phosgene solution (purum, ˜20% in toluene, 0.48 mL, 0.91 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 16 h followed by the addition of saturated aqueous sodium bicarbonate solution. The mixture was extracted with dichloromethane (30 mL), washed with water and brine, dried over sodium sulfate, filtered, concentrated to small volume, and triturated with diethyl ether (5 mL) to precipitate the product. The solid was collected by filtration, washed with water (3×5 mL) and hexanes (5 mL), and dried in vacuo to afford ethyl 4-methyl-2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)thiazole-5-carboxylate as a white solid (0.21 g, 80% yield): MS (ES+) m/z 304.2 (M+1).

Workup

  1. extractionThe mixture was extracted with dichloromethane (30 mL)
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to small volume
  6. customtriturated with diethyl ether (5 mL)
  7. customto precipitate the product
  8. filtrationThe solid was collected by filtration
  9. washwashed with water (3×5 mL) and hexanes (5 mL)
  10. customdried in vacuo

Sources & evidence

ORD record
ord-2a32e50f7e144e4599df4127f5c4b57c
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

Loading…