Triethylamine → HCID 21201727, compound

HRID 1979449Notes

Reaction equation

HRID 1979449 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].ClC(Cl)(O[C:17](=[O:23])OC(Cl)(Cl)Cl)Cl.C([N:27](CC)CC)C.[C:32]1([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[C:48]([CH3:51])[CH:49]=[CH:50][C:45]=3[N:44]([C:52](=[O:58])[C:53]3[S:57][CH:56]=[CH:55][CH:54]=3)[CH2:43][CH:42]([NH2:59])[C:41]2=[O:60])=[O:38])[S:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.C(Cl)(Cl)Cl.O>[C:32]1([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[C:48]([CH3:51])[CH:49]=[CH:50][C:45]=3[N:44]([C:52](=[O:58])[C:53]3[S:57][CH:56]=[CH:55][CH:54]=3)[CH2:43][CH:42]([NH:59][C:17]([NH:27][C:12]3[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][CH:2]=3)=[O:23])[C:41]2=[O:60])=[O:38])[S:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 21201778HCID 21201778, compound

Product 1

HCID 21201727HCID 21201727, compoundYield 200.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
6.5 °C

Procedure

Ethyl 3-aminobenzoate (0.54 g) was dissolved in tetrahydrofuran (15 ml), the solution was cooled to internal temperature 5-8° C. Triphosgene (0.35 g) was added, the mixture was stirred for 5 minutes. Subsequently, triethylamine (1.20 g) was added to the mixture over 15 minutes interval, stirred at room temperature for 10 minutes, and a solution of 1-(2-thenoylmethyl)-2-oxo-3-amino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.26 g) in tetrahydrofuran (15 ml) was added, stirred for one hour. Water and chloroform were added to the reaction mixture, and extracted. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, crystals so precipitated were collected by filtration with ether, to thereby obtain 1.46 g of the title compound (Yield: 79.8%).

Workup

  1. stirringstirred at room temperature for 10 minutes
  2. stirringstirred for one hour
  3. extractionextracted
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure, crystals
  7. customso precipitated
  8. filtrationwere collected by filtration with ether

Sources & evidence

ORD record
ord-634cd86108f94361bc8be7f861a8ee12
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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