1,2-Dichloroethane → HCID 57216072, compound

HRID 1934647Notes

Reaction equation

HRID 1934647 reaction equation
O[CH2:2][C@@H:3]([NH:6][C:7]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:8]=1[C:9]([NH:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1)=[O:10])[CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:48]CCCl>C(Cl)(Cl)(Cl)Cl>[Cl:48][CH2:2][C@@H:3]([NH:6][C:7]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:8]=1[C:9]([NH:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1)=[O:10])[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 11776TriphenylphosphineHCID 53643440HCID 53643440, compound

Product 1

HCID 57216072HCID 57216072, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of (S)-2-[1-(hydroxymethyl)propylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (127 mg) in 1,2-dichloroethane (4 mL) and carbontetrachloride (2 mL) was added triphenylphosphine (215 mg), and the mixture was stirred for an hour under reflux. The solvent was evaporated in vacuo and the residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and ethyl acetate (9:1) to give (S)-2-[1-(chloromethyl)propylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (71 mg) as a solid substance.

Workup

  1. temperatureunder reflux
  2. customThe solvent was evaporated in vacuo
  3. washeluting with a mixture of chloroform and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-fc2b1e52a0264d099bd17bfa22d03b7e
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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