Dimethylformamide → HCID 86747159, compound

HRID 2255294Notes

Reaction equation

HRID 2255294 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=N)=[CH:6][CH:5]=1.C[N:14](C=O)C.[C:18]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19]1>CN(C1C=CC=CN=1)C.N1C=CC=CC=1>[NH2:14][N:10]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([NH:3][CH:21]([CH:22]=[O:23])[CH2:20][CH2:19][C:18]([OH:24])=[O:25])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7940Glutaric anhydrideHCID 756264-Amidinoaniline dihydrochloride

Product 1

HCID 86747159HCID 86747159, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

4-Aminobenzamidine di-HCl (1 g, 4.8 mmol) was added to dry DMF (20 mL). To this solution dry pyridine (5 mL) and glutaric anhydride (0.68 g, 5.3 mmol) followed by 10 mg dimethylaminopyridine (DMAP) were added. The product started to precipitate after heating for 1/2h at 100° C. Heating was continued for 2 hr and water (25 mL) was added after cooling to room temperature. An abundant precipitate was filtered and dried in a desiccator to give 0.8 g, 50% of product as a white solid: H NMR (d6 -DMSO) δ 1.95 (m, 2H), 2.4 (m, 2H), 2.5 (m, 2H), 7.85 (s, 4H), 9.05 (bs, 2H), 9.25 (bs, 2H), 10.4 (s, 1H), MS(FAB) m/e 250.1 (M+H+).

Workup

  1. additionwere added
  2. customto precipitate
  3. temperatureHeating
  4. additionwater (25 mL) was added
  5. temperatureafter cooling to room temperature
  6. filtrationAn abundant precipitate was filtered
  7. customdried in a desiccator

Sources & evidence

ORD record
ord-726d6dd32cb14a91b3945e2f276e5b66
Source dataset
uspto-grants-1993_08
Patent number
US05239113

Reaction notes

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