Triethylamine → HCID 20291876, compound

HRID 1413344Notes

Reaction equation

HRID 1413344 reaction equation
C(N(CC)CC)C.[N-:8]=[N+:9]=[N-:10].[Na+].[N+]([C:15]1[CH:34]=[CH:33][CH:32]=[C:17]2[C:18]([N:20]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[C:21](=[O:22])[C:16]=12)=[O:19])([O-])=O>CS(C)=O>[N:8]([C:32]1[CH:33]=[CH:34][CH:15]=[C:16]2[C:21]([N:20]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[C:18](=[O:19])[C:17]=12)=[O:22])=[N+:9]=[N-:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 30900094-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzoic acid

Product 1

HCID 20291876HCID 20291876, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

1.4 ml (0.01 mol) of triethylamine, followed by 0.72 g (0.011 mol) of sodium azide, are added to a mixture of 3.12 g (0.01 mol) of 4-(3-nitrophthalimidyl)-benzoic acid and 20 ml of dimethylsulphoxide. The reaction mixture is heated for 6 hours at 50° C. and is then evaporated in vacuo at 80° C.; the residue is stirred with 70 ml of water and the resulting solution is then brought to pH 1 with hydrochloric acid. The product which has precipitated is filtered off with suction, washed with 5 ml of methanol and dried for 24 hours in a drying cabinet at 80° C./100 mm Hg. 2.47 g (80% of theory) of 4-(3-azidophthalimidyl)-benzoic acid are obtained; melting point 300° C. (with decomposition). IR spectrum (KBr): 1790 and 1740 cm-1 (CO--N--CO); 2150 cm-1 (N3).

Workup

  1. customis then evaporated in vacuo at 80° C.
  2. customThe product which has precipitated
  3. filtrationis filtered off with suction
  4. washwashed with 5 ml of methanol
  5. customdried for 24 hours in a drying cabinet at 80° C./100 mm Hg

Sources & evidence

ORD record
ord-0fc3947eea604b96872a00b7b302f992
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

Loading…