Putrescine → Benzoic acid, 4,4'-[1,4-butanediylbis(iminocarbonyl)]bis-, dimethyl ester

HRID 326200Notes

Reaction equation

HRID 326200 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[CH2:14]([NH2:19])[CH2:15][CH2:16][CH2:17][NH2:18]>C1(C)C=CC=CC=1.O>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:19][C:9](=[O:10])[C:8]2[CH:7]=[CH:6][C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 1045PutrescineHCID 81850Methyl 4-(chlorocarbonyl)benzoate

Product 1

HCID 3277465Benzoic acid, 4,4'-[1,4-butanediylbis(iminocarbonyl)]bis-, dimethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

4-Carbomethoxybenzoyl chloride (19.07 g, 0.096 mol) was dissolved in toluene (380 mL) in a 3-necked, 1000 mL round-bottomed flask equipped with mechanical stirrer, thermometer, and addition funnel A solution of 1,4-butanediamine in water (80 mL) was added dropwise over a period of 40 minutes while the temperature of the reaction mixture was maintained at 25° C. by a water bath. A white solid formed immediately and the reaction mixture stirred for an additional 2 hours. The solid was collected on a frit and washed with toluene, water, 5% HCl, and water. Recrystallization from DMF gave white crystals which were dried in a vacuum oven at 60° C.; yield 17.91 g (90%); m.p. 260°-261° C. 1H NMR (200 MHz, DMSO-d6) δ8.70 (2H, m), 8.05-7.93 (8H, m) 3.88 (6H, s) 3.34 (4H, s), 1.58 (4H, s); IR (nujol) 3300, 1720, 1625, 1530, 1275, 1105, 860, 730 cm-1 ; low res. MS (CI, isobutane) 413 (MH+); 13C NMR (75 MHZ, DMSO-d6) δ166.9, 165.7, 165.4, 165.2, 138.7, 131.6, 129.0, 127.5, 127.2, 52.3, 26.5.

Workup

  1. customequipped with mechanical stirrer
  2. additionwas added dropwise over a period of 40 minutes while the temperature of the reaction mixture
  3. customA white solid formed immediately
  4. customThe solid was collected on a frit
  5. washwashed with toluene, water, 5% HCl, and water
  6. customRecrystallization from DMF
  7. customgave white crystals which
  8. customwere dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-8d57243d1a204ce586e4d4e224ed6561
Source dataset
uspto-grants-1993_12
Patent number
US05268003

Reaction notes

Loading…