Toluene → HCID 57785870, compound

HRID 1628995Notes

Reaction equation

HRID 1628995 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[N:16]([CH2:17][CH2:18][OH:19])[C:15]2[C:20]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:21][CH:22]=[CH:23][C:14]=2[N:13]=1)(O)[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH3:10])[C:12]2=[N:13][C:14]3[C:15](=[C:20]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH:21]=[CH:22][CH:23]=3)[N:16]2[CH2:17][CH2:18][O:19]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68772198HCID 68772198, compound

Product 1

HCID 57785870HCID 57785870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(2,4-dichlorophenyl)-1-[7-(diethylamino)-1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]ethanol (Reference example 210, 63.8 mg, 0.151 mmol) and triphenylphosphine (59.4 mg, 0.227 mmol) in tetrahydrofuran (4 mL) was added a solution of diethyl azodicarboxylate in toluene (40%, 103 μL, 0.227 mmol) at room temperature. After 2.5 h, the reaction mixture was concentrated in vacuo, and purified by column chromatography on silica gel eluting with a 0-20% ethyl acetate/n-hexane gradient mixture to give a colorless amorphous (53.3 mg, 0.132 mmol, 87%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography on silica gel eluting with a 0-20% ethyl acetate/n-hexane gradient mixture
  3. customto give a colorless amorphous (53.3 mg, 0.132 mmol, 87%)

Sources & evidence

ORD record
ord-7655d43bf9de41ac915afc36495de145
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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