1,2-Dichloroethane → HCID 178519372, compound

HRID 1908999Notes

Reaction equation

HRID 1908999 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C.C(Cl)CCl>CN(C)C1C=CN=CC=1.CN(C=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[O:12])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 178524171HCID 178524171, compound

Product 1

HCID 178519372HCID 178519372, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1H-benzoimidazole-5-carboxylic acid (10 g, 61.7 mmol), morpholine (7.55 mL, 86.3 mmol), ethyldiisopropylamine (16.1 mL, 92.5 mmol) and 4-dimethylaminopyridine (380 mg, 3.08 mmol) in DMF (60 mL) at room temperature was added EDC (12.4 g, 64.8 mmol) in a single portion. The mixture was stirred at room temperature for 3 days then concentrated in vacuo. The product was purified by recrystallisation from acetonitrile (70 mL), providing (1H-benzoimidazol-5-yl)-morpholin-4-yl-methanone (8.7 g).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe product was purified by recrystallisation from acetonitrile (70 mL)

Sources & evidence

ORD record
ord-b81038e0249d4d3ab83094ccccc9f797
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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