Hydrochloric Acid → HCID 13457007, compound

HRID 482950Notes

Reaction equation

HRID 482950 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=O)=[CH:16][C:3]1=2.S(Cl)(Cl)=O.Cl.[NH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][OH:29]>CN(C)C=O.C(Cl)Cl.O>[OH:29][CH2:28][C:27]([NH:26][C:18](=[O:20])[CH2:17][C:15]1[CH:14]=[CH:13][C:4]2[O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[C:3]=2[CH:16]=1)([CH3:31])[CH3:30]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 118072-Amino-2-methyl-1-propanolHCID 24386Thionyl ChlorideHCID 41448Isoxepac

Product 1

HCID 13457007HCID 13457007, compoundYield 41.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A water cooled stirred suspension of 13.41 g (0.05 mol) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl acetic acid, 50 ml of sieve-dried methylene chloride and three drops of dimethylformamide was treated for a few minutes with 6.54 g (0.055 mol) of thionyl chloride. After total addition the suspension was stirred 15 minutes with cooling and was then intermittently warmed until the evolution of HCl ceased. A stirred ice water chilled solution of 13.37 g (0.15 mol) of 2-amino-2-methyl-1-propanol and 50 ml of sieve-dried methylene chloride was treated dropwise over 0.5 hour with the acid chloride solution. After total addition the resultant suspension was stirred with cooling for 20 minutes and was then stirred 1.5 hours at ambient temperature. The suspension was vacuum filtered and the filtrate was washed with 100 ml each of 5% HCl, water, and 5% Na2CO3. The organic phase was dried by extracting with 500 ml of saturated NaCl solution and then over anhydrous Na2SO4. The resultant mixture was filtered and the filtrate was concentrated to an oil which was dried by azeotropic distillation of absolute ethanol to afford 14.3 g (84.3%) of a crude product. Two recrystallizations from benzene and a final recrystallization from isopropanol afforded 7.0 g (41.2%) of crystals of 6,11-dihydro-N-(1-hydroxy-2-methyl-2-propyl)-11-oxodibenz[b,e]oxepin-2-yl acetamide, m.p. 132°-134° C.

Workup

  1. additionAfter total addition the suspension
  2. stirringwas stirred 15 minutes
  3. temperaturewith cooling
  4. stirringwas stirred
  5. temperaturewith cooling for 20 minutes
  6. stirringwas then stirred 1.5 hours at ambient temperature
  7. filtrationfiltered
  8. washthe filtrate was washed with 100 ml each of 5% HCl, water, and 5% Na2CO3
  9. customThe organic phase was dried
  10. extractionby extracting with 500 ml of saturated NaCl solution
  11. filtrationThe resultant mixture was filtered
  12. concentrationthe filtrate was concentrated to an oil which
  13. dry with materialwas dried by azeotropic distillation of absolute ethanol
  14. customto afford 14.3 g (84.3%) of a crude product
  15. customTwo recrystallizations from benzene
  16. customa final recrystallization from isopropanol

Sources & evidence

ORD record
ord-6fbca52bfa1e454989f709d4125a399d
Source dataset
uspto-grants-1986_03
Patent number
US04576960

Reaction notes

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