HCID 20450000, compound → HCID 20450013, compound

HRID 358052Notes

Reaction equation

HRID 358052 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]S(=O)(=O)[CH:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:11]=2[CH:28]=1)=[O:5])[CH3:2]>C(Cl)(Cl)(Cl)Cl.C(O)(C)(C)C.O>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:12]1[C:11]2[CH:28]=[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=[CH:9][C:10]=2[NH:17][C:16](=[O:18])[CH2:15][CH:14]=1

Participants

5

Reactant 1

HCID 20450000HCID 20450000, compound

Product 1

HCID 20450013HCID 20450013, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6386tert-ButanolSolvent

Procedure

93.1 g of 8-(ethoxycarbonylamino)-6-(2-chlorophenyl)-1,3,4,6-tetrahydro-2-oxo-2H-5,1-benzothiazocine 5,5-dioxide are dissolved at 80° in a mixture of 1.3 l of carbon tetrachloride, 1.3 l of t-butanol and 33.5 ml of water. After cooling to 35°, the mixture is treated rapidly with 212 g of potassium t-butylate (in three portions) while cooling strongly. The temperature thereby rises to 45°-50°. After the reaction has faded away, the cooling bath is removed and the mixture is stirred for a further 30 minutes. The mixture is poured on to ice and extracted several times with chloroform. The organic solvents are evaporated and the residue is chromatographed on 310 g of silica gel. The desired product is eluted with toluene/chloroform (1:3). After recrystallization from ethyl acetate/petroleum ether, there is obtained ethyl 5-(2-chlorophenyl)-2,3-dihydro-2-oxo-1H-1-benzazepine-7-carbamate of melting point 241°.

Workup

  1. temperatureAfter cooling to 35°
  2. temperaturewhile cooling strongly
  3. customthereby rises to 45°-50°
  4. customthe cooling bath is removed
  5. additionThe mixture is poured on to ice
  6. extractionextracted several times with chloroform
  7. customThe organic solvents are evaporated
  8. customthe residue is chromatographed on 310 g of silica gel
  9. washThe desired product is eluted with toluene/chloroform (1:3)
  10. customAfter recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-da4912fc28504ba59544f1ad373aa1bb
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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