Ammonia → HCID 14994971, compound

HRID 1769736Notes

Reaction equation

HRID 1769736 reaction equation
Br[CH:2]([CH3:29])[C:3]([NH:5][C:6]1[S:19][C:9]2[CH2:10][N:11]([C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])=[O:4].[NH3:30].Cl>ClCCCl.C(OCC)(=O)C>[NH2:30][CH:2]([CH3:29])[C:3]([NH:5][C:6]1[S:19][C:9]2[CH2:10][N:11]([C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])=[O:4]

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 14994970HCID 14994970, compound

Product 1

HCID 14994971HCID 14994971, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

23.04 g of 2-(2-bromopropionylamino)-3-(2-chlorobenzoyl)-6-cyclopropanecarbonyl-4,5,6,7-tetrahydro-thieno[2,3-C]pyridine was dissolved in 65 ml of 1,2dichloroethane and 65 ml of ethyl acetate, into which ammonia gas was passed at -15° C. for 1 hour. This solution was placed in a sealed tube and reacted at 110° C. for 2 hours. In order to complete the reaction, ammonia was again passed into the solution at -15° C. for 30 minutes in the sealed tube where the reaction was continued at 110° C. for 1.5 hours. After ice-cooling, the reaction solution was charged into ice-cooled 2N hydrochloric acid, to which ethyl acetate was added, from which the resultant aqueous phase was collected. Sodium carbonate was added to the aqueous phase under ice-cooling conditions so that the pH was adjusted to 8, followed by extracted with chloroform under salting-out conditions. The extract was washed with a saturated saline solution and dried with anhydrous magnesium sulfate, followed by filtration and concentration to obtain 12.97 g (yield 64%) of the intended compound.

Workup

  1. customThis solution was placed in a sealed tube
  2. customreacted at 110° C. for 2 hours
  3. waitthe reaction was continued at 110° C. for 1.5 hours
  4. temperatureAfter ice-cooling
  5. additionthe reaction solution was charged into ice-
  6. customwas collected
  7. additionSodium carbonate was added to the aqueous phase under ice-
  8. temperaturecooling conditions so that the pH
  9. extractionby extracted with chloroform under salting-out conditions
  10. washThe extract was washed with a saturated saline solution
  11. dry with materialdried with anhydrous magnesium sulfate
  12. filtrationfollowed by filtration and concentration

Sources & evidence

ORD record
ord-b299defe145946c1909941730dcd9519
Source dataset
uspto-grants-1995_01
Patent number
US05382579

Reaction notes

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