Thionyl Chloride → HCID 13457009, compound

HRID 482951Notes

Reaction equation

HRID 482951 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7](=O)[CH2:8][C:9]1[CH:24]=[CH:23][C:12]2[O:13][CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17](=[O:18])[C:11]=2[CH:10]=1)([CH3:5])[CH3:4].S(Cl)(Cl)=O>C(Cl)Cl>[O:18]=[C:17]1[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[CH2:14][O:13][C:12]2[CH:23]=[CH:24][C:9]([CH2:8][C:7]3[O:1][CH2:2][C:3]([CH3:5])([CH3:4])[N:6]=3)=[CH:10][C:11]1=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13457007HCID 13457007, compound

Product 1

HCID 13457009HCID 13457009, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, ice water cooled mixture of 10.25 g (0.0302 mol) of 6,11-dihydro-N-(1-hydroxy-2-methyl-2-propyl)-11-oxodibenz[b,e]oxepin-2-yl acetamide of Example 2, and 100 ml of sieve dried CH2Cl2 was treated dropwise over a few minutes with 3.95 g (0.0332 mol) of thionyl chloride. The solution was then stirred 15 minutes with cooling and overnight (about 16 hours) at ambient temperature. The solution was washed with 10% sodium hydroxide solution, dried (Na2SO4) and concentrated to an oil which was dried by azeotropic distillation of toluene. On standing overnight at 5° C. the oil crystallized. Recrystallization from 12 ml of isopropanol afforded 6.10 g (62.9%) of crystals of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin2-yl)methyl-4,4-dimethyloxazoline, m.p. 101°-103.5° C.

Workup

  1. washThe solution was washed with 10% sodium hydroxide solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to an oil which
  4. dry with materialwas dried by azeotropic distillation of toluene
  5. waitOn standing overnight at 5° C.
  6. customthe oil crystallized
  7. customRecrystallization from 12 ml of isopropanol

Sources & evidence

ORD record
ord-5975b43674634f83b822d7947a26e46e
Source dataset
uspto-grants-1986_03
Patent number
US04576960

Reaction notes

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