N-Hydroxysuccinimide → HCID 86655524, compound

HRID 1746583Notes

Reaction equation

HRID 1746583 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=[O:9])#[N:2].O[N:15]1[C:19](=[O:20])[CH2:18][CH2:17][C:16]1=[O:21].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]([O:10][N:15]2[C:19](=[O:20])[CH2:18][CH2:17][C:16]2=[O:21])=[O:9])[CH:11]=[CH:12][CH:13]=1)#[N:2]

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 447258693-(3-Cyanophenyl)-2-propenoic acid

Product 1

HCID 86655524HCID 86655524, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methylene chloride (300 mL) suspension of 3-cyanocinnamic acid (9.0 g) and N-hydroxysuccinic acid imide (9.0 g) was added WSC.HCl (15.0 g) at 0° C., and the mixture was stirred for 6 hours at room temperature. The reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulfate. The crystals obtained by distilling off the solvent under a reduced pressure were filtered with diethyl ether, to give the captioned compound (13.0 g, 93%).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe crystals obtained
  4. distillationby distilling off the solvent under a reduced pressure
  5. filtrationwere filtered with diethyl ether

Sources & evidence

ORD record
ord-6d0c7a0dd4f5499a9c92d5011c848595
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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