Methanol → HCID 131727635, compound

HRID 733513Notes

Reaction equation

HRID 733513 reaction equation
C([NH:8][CH2:9][C:10]1[CH:20]=[CH:19][C:13]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=C[CH:11]=1)(OC(C)(C)C)=O.S(Cl)([Cl:23])=O.[CH3:25]O>>[ClH:23].[NH2:8][CH2:9][CH:10]([CH3:11])[CH2:20][CH2:19][CH2:13]/[CH:14]=[CH:15]/[C:16]([O:18][CH3:25])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 69501606HCID 69501606, compound

Product 1

HCID 131727635HCID 131727635, compoundYield 86%

Procedure

To a mixture of 4-(N-Boc-aminomethyl) cinnamic acid (5 g, 0.018 mol) in methanol (200 mL) was added thionylchloride (11 g) at 0° C. and slowly heated to reflux for 3 h. The reaction mixture was concentrated to give solid product. The solid hydrochloride salt was washed with EtOAc and filtered off to give the title compound (3.5 g, 86%).

Workup

  1. temperatureslowly heated
  2. temperatureto reflux for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. customto give solid product
  5. washThe solid hydrochloride salt was washed with EtOAc
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-4b90488f6e204aa995184b0690856a2a
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

Loading…