Thionyl Chloride → HCID 19352280, compound

HRID 726882Notes

Reaction equation

HRID 726882 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH:13]([N:17]([CH3:28])[C:18]([O:20]CC1C=CC=CC=1)=[O:19])[C:14]([OH:16])=O.S(Cl)(Cl)=O>CCCCCC>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH:13]1[C:14](=[O:16])[O:20][C:18](=[O:19])[N:17]1[CH3:28]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19352278HCID 19352278, compound

Product 1

HCID 19352280HCID 19352280, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

18.5 g of 4-(2,3-dimethoxyphenyl)-2-(N-methyl-N-benzyloxycarbonyl-amino)-butyric acid (0.048 mole) and 28.7 g of thionyl chloride are placed into a 250 ml round-bottomed flask, refluxing for 2 hours then distilling off under vacuum the thionyl chloride until obtaining a thick oil. The oil is taken up into 100 ml of hexane, stirring until solidification, then it is decanted and triturated with 100 ml more of hexane, filtered and dried under vacuum at 30° C. to obtain a fine crystalline powder. Yield: 12.5 g, 93% (moles), 68% (weight).

Workup

  1. temperaturerefluxing for 2 hours
  2. distillationthen distilling off under vacuum the thionyl chloride
  3. customuntil obtaining a thick oil
  4. customit is decanted
  5. customtriturated with 100 ml more of hexane
  6. filtrationfiltered
  7. customdried under vacuum at 30° C.
  8. customto obtain a fine crystalline powder

Sources & evidence

ORD record
ord-9495468df6cb4381955d6a45ce0f8617
Source dataset
uspto-grants-1998_01
Patent number
US05710336

Reaction notes

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