1,1'-Carbonyldiimidazole → (Benzo[d][1,3]dioxol-4-yl)methyl 1h-imidazole-1-carboxylate

HRID 2062202Notes

Reaction equation

HRID 2062202 reaction equation
[O:1]1[C:5]2[C:6]([CH2:10][OH:11])=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[N:12]1([C:17](N2C=CN=C2)=[O:18])[CH:16]=[CH:15][N:14]=[CH:13]1>C(Cl)Cl>[N:12]1([C:17]([O:11][CH2:10][C:6]2[C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=[CH:8][CH:7]=2)=[O:18])[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 2776187(1,3-Dioxaindan-4-yl)methanol

Product 1

HCID 58010871(Benzo[d][1,3]dioxol-4-yl)methyl 1h-imidazole-1-carboxylateYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (benzo[d][1,3]dioxol-7-yl)methanol (2.0 g, 13.1 mmol) and di(1H-imidazol-1-yl)methanone (4.26 g, 26.2 mmol) in 20 mL CH2Cl2 was heated overnight at 50° C. The reaction was quenched with water and extracted with CH2Cl2, and the combined layers were dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 10-70% EtOAc in CH2Cl2 gave (benzo[d][1,3]dioxol-7-yl)methyl 1H-imidazole-1-carboxylate (2.8 g, 86%). 1H NMR (400 MHz, CDCl3) δ 8.15 (t, J=0.9 Hz, 1H), 7.44 (t, J=1.4 Hz, 1H), 7.07 (dd, J=1.6, 0.8 Hz, 1H), 6.95 (m, 2H), 6.84 (m, 1H), 6.01 (s, 2H), 5.33 (s, 2H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2
  3. dry with materialthe combined layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-944f16a72ba241de89083459885f1b04
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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