Chloroform → HCID 53750214, compound

HRID 325550Notes

Reaction equation

HRID 325550 reaction equation
[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].C(Cl)(Cl)[Cl:16].C(=O)([O-])[O-].[Na+].[Na+].[C:25](Cl)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O>[C:25]([N:4]([CH2:1][CH:2]=[CH2:3])[C:5]1[CH:6]=[C:7]([CH2:11][C:12]([Cl:16])=[O:14])[CH:8]=[CH:9][CH:10]=1)([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 13293047HCID 13293047, compound

Product 1

HCID 53750214HCID 53750214, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. 3-(allylamino)phenylacetic acid in 200 ml. warm chloroform is added a solution of 12 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid, dried, and evaorated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time ultimately to yield 3-(N-carbobenzyloxy-allylamino)phenylacetyl chloride as a viscous, orange oil.

Workup

  1. additionTo the vigorously stirred solution is added 10 g
  2. customthe layers are separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. dissolutionThe oil is dissolved in 300 ml
  6. additiontoluene, treated with 15 ml
  7. temperaturethionyl chloride and the solution is refluxed for 5 hours
  8. customThe solvents are evaporated
  9. dissolutionthe residue is dissolved three times in toluene
  10. customevaporating each time ultimately

Sources & evidence

ORD record
ord-e2ed7dc0f5db4dd69e4794f6724f8ae4
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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