Triethylamine → HCID 54394968, compound

HRID 2266778Notes

Reaction equation

HRID 2266778 reaction equation
[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25]O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(Cl)([Cl:36])=O>C1(C)C=CC=CC=1>[Cl:36][CH2:25][C:21]1[N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11131622HCID 11131622, compound

Product 1

HCID 54394968HCID 54394968, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (1-trityl-1H-imidazol-2-yl)-methanol (9.92 g; CAS 102152-03-4) in toluene (160 ml) was cooled under an argon atmosphere to 0° C. and treated with triethylamine (8.1 ml). Then, thionylchloride (2.96 ml) was added dropwise. The reaction mixture was stirred for 1 hour at 0° C., then treated with 500 ml ice-cold H2O. The mixture was extracted with EtOAc. The organic layer was washed with H2O, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (silica gel; eluent: CH2Cl2/methanol 95:5) to give 2-chloromethyl-1-trityl-1H-imidazole (2.73 g) as off-white solid. MS 359.0 ([M+H]+)

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel; eluent: CH2Cl2/methanol 95:5)

Sources & evidence

ORD record
ord-b81a24bff927406dad200f0232963b1e
Source dataset
uspto-grants-2010_12
Patent number
US07858653B2

Reaction notes

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