1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67022252, compound

HRID 2198049Notes

Reaction equation

HRID 2198049 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=O.[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([N:15]2[CH2:20][CH2:19][S:18][CH2:17][CH2:16]2)=[O:7])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67164ThiomorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 110867883-Bromo-5-(trifluoromethyl)benzoic acid

Product 1

HCID 67022252HCID 67022252, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-bromo-5-(trifluoromethyl)benzoic acid (10 g), thiomorpholine (5.0 g), HOBt (7.4 g) and EDCI (9.26 g) in acetonitrile (113 ml) was stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to give the title compound (12.3 g, yield 94%) a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-950a0b1087f44fcaabebfe915c619fcf
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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