Ammonia → HCID 136351306, compound

HRID 963070Notes

Reaction equation

HRID 963070 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=1[C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[O:4].[I-].[Na+].[NH3:27]>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:6]=2[NH:5][C:3](=[O:4])[CH2:2][N:27]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5238Sodium IodideHCID 19085208HCID 19085208, compound

Product 1

HCID 136351306HCID 136351306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

Ethyl 5-(2-chloroacetylamino)-4-(2-chlorobenzoyl)thiophene-2-carboxylate (325 g) and sodium iodide (151.3 g) were added to tetrahydrofuran (3500 ml), and the mixture was refluxed under heating for 1.5 hours. The mixture was cooled to -65° C., and ammonia (164 ml) was added. The reaction temperature was raised slowly to room temperature. The solvent was evaporated, and chloroform and water were added. The organic layer was taken out, washed with water and dried over sodium sulfate. The solvent was evaporated. Toluene (7 l) and silica gel (1365 g) were added thereto, and the mixture was refluxed under heating for 1.5 hours. The silica gel was collected by filtration, and a mixed solvent of chloroform-methanol (10:1) was added to elute the obtained product. The solvent was evaporated, and ethyl acetate was added. The resulting crystals were collected by filtration and washed with ethyl acetate to give 70.0 g of ethyl (5-(2-chlorophenyl)-1,2-dihydro-3H-thieno[2,3-e] [1,4]diazepin-2-on-7-yl)-carboxylate.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1.5 hours
  3. temperatureThe reaction temperature was raised slowly to room temperature
  4. customThe solvent was evaporated
  5. additionchloroform and water were added
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated
  9. additionToluene (7 l) and silica gel (1365 g) were added
  10. temperaturethe mixture was refluxed
  11. temperatureunder heating for 1.5 hours
  12. filtrationThe silica gel was collected by filtration
  13. additiona mixed solvent of chloroform-methanol (10:1) was added
  14. washto elute the obtained product
  15. customThe solvent was evaporated
  16. additionethyl acetate was added
  17. filtrationThe resulting crystals were collected by filtration
  18. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-cc78d1f08cf745d5a2b7c8a1774fbe66
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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