Dichloromethane → HCID 13340644, compound

HRID 1981308Notes

Reaction equation

HRID 1981308 reaction equation
O[CH2:2][C:3]([NH:6][C:7](=[O:24])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:18][CH2:17][C:16]3[CH:19]=[CH:20][S:21][C:15]=3[C:14](=[O:22])[C:13]=2[CH:23]=1)([CH3:5])[CH3:4].O=S(Cl)Cl.[CH2:29](Cl)Cl>>[CH:17]([O:18][CH:12]([CH3:11])[CH3:13])([CH3:16])[CH3:29].[O:22]=[C:14]1[C:13]2[CH:23]=[C:9]([CH2:8][C:7]3[O:24][CH2:5][C:3]([CH3:4])([CH3:2])[N:6]=3)[CH:10]=[CH:11][C:12]=2[O:18][CH2:17][C:16]2[CH:19]=[CH:20][S:21][C:15]1=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 13340643HCID 13340643, compound

Product 2

HCID 7914Diisopropyl EtherHCID 13340644HCID 13340644, compoundYield 52%

Procedure

To a suspension of 8.3 g (0.02 m) of 4,10-dihydro-N-(1-hydroxy-2-methyl-2-propyl)-10-oxothieno[3,2-c][1]benzoxepin-8-yl acetamide of Example 1 and 200 ml of methylene chloride, SOCl2 (3.09 g) was added dropwise keeping the temperature at approximately 5° C. The suspended material gradually dissolved. The mixture was stirred overnight (about 16 hours). The organic layer was washed with 10% NaOH, dried (Na2SO4) and evaporated to give an oil. Trituration with isopropyl ether gave 4.1 g (52%) of 2-(4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-yl)methyl-4,4-dimethyl-oxazoline, m.p. 85°-87° C.

Workup

  1. additionwas added dropwise
  2. customat approximately 5° C
  3. dissolutionThe suspended material gradually dissolved
  4. washThe organic layer was washed with 10% NaOH
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil

Sources & evidence

ORD record
ord-b260a6e6248b41cba33d4efe729939a3
Source dataset
uspto-grants-1985_04
Patent number
US04514411

Reaction notes

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