Triethylamine → HCID 20291877, compound

HRID 1413346Notes

Reaction equation

C(N(CC)CC)C.[N-:8]=[N+:9]=[N-:10].[Na+].[N+]([C:15]1[CH:33]=[CH:32][CH:31]=[C:17]2[C:18]([N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:21](=[O:22])[C:16]=12)=[O:19])([O-])=O>CS(C)=O>[N:8]([C:31]1[CH:32]=[CH:33][CH:15]=[C:16]2[C:21]([N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:18](=[O:19])[C:17]=12)=[O:22])=[N+:9]=[N-:10]

Participants

Conditions

Temperature: 50 °C

Procedure

2.58 ml (0.018 mol) of triethylamine, followed by 1.3 g (0.0198 mol) of sodium azide, are added to a mixture of 5.7 g (0.018 mol) of 6-(3-nitrophthalimidyl)-caproic acid in 35 ml of dimethylsulphoxide. The reaction mixture is heated for 6 hours at 50° C. and is then concentrated in vacuo, diluted with 100 ml of water and acidified with 4 ml of concentrated hydrochloric acid. The resulting suspension of the reaction product is stirred for 18 hours and filtered with suction, and the filter residue is washed with 20 ml of water and dried for 24 hours at 60° C./0.100. mm Hg, over phosphorus pentoxide. 5.1 g (94% of theory) of 6-(3-azidophthalimidyl)-caproic acid are obtained; melting point 87°-90° C. (with decomposition). IR spectrum (CH2Cl2): 1780 and 1725 cm-1 (CO--N--CO); 2130 cm-1 (N3).

Workup

concentrationis then concentrated in vacuo
additiondiluted with 100 ml of water
additionThe resulting suspension of the reaction product
filtrationfiltered with suction
washthe filter residue is washed with 20 ml of water
customdried for 24 hours at 60° C./0.100

Sources & evidence

ORD record: ord-b3148f537cf5496c8ccd06d8e655dec5
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04250096

Reaction notes

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