1,1'-Carbonyldiimidazole → HCID 62588378, compound

HRID 1435572Notes

Reaction equation

HRID 1435572 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][OH:25]>CN(C)C=O>[OH:25][CH2:24][C:23]1[CH:22]=[C:21]([NH:20][C:5](=[O:7])[CH2:4][CH2:3][O:2][CH3:1])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 802933-Aminobenzyl alcoholHCID 1344423-Methoxypropionic acid

Product 1

HCID 62588378HCID 62588378, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.76 g (7.31 mmol) 3-methoxypropionic acid in 10 ml dry N,N-dimethylformamide (DMF) were treated with 1.25 g (7.71 mmol) 1,1′-carbonyl-diimidazole and stirred for 1 hr at room temperature. 1.00 g 3-aminobenzylalcohol were added and stirring was continued over night. The solvent was removed and the residue chromatographed on silica in ethyl acetate, yielding 1.26 g N-(3-Hydroxymethyl-phenyl)-3-methoxy-propionamide.

Workup

  1. stirringstirring
  2. waitwas continued over night
  3. customThe solvent was removed
  4. customthe residue chromatographed on silica in ethyl acetate

Sources & evidence

ORD record
ord-fbb9079edfc8419782141be44060d535
Source dataset
uspto-grants-2009_11
Patent number
US07618964B2

Reaction notes

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