tert-Butanol → HCID 18956271, compound

HRID 1656015Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)([CH2:12][CH2:13][CH2:14][CH3:15])[C:9](O)=[O:10])=[CH:4][CH:3]=1.C(O)(C)(C)C.C1(P([N:41]=[N+:42]=[N-:43])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)([CH2:12][CH2:13][CH2:14][CH3:15])[C:9]([N:41]=[N+:42]=[N-:43])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1.0 g (3.25 mmols) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoic acid in 3 mL of dimethylformamide was added 0.30 mL of tert-butanol. This solution was cooled to 0° C. and a solution of 1.07 g (3.90 mmols) of diphenylphosphorylazide in 1 mL of dimethylformamide was added followed by 0.72 mL (7.15 mmols) of triethylamine. The resultant mixture was stirred for 2 hours and then allowed to warm to room temperature and stirred for an additional 15 hours. Addition of ice caused the precipitation of the product. Filtration gave 1.10 g of a crude product which was carefully recrystallized from a 1 to 3 mixture of ethyl acetate and hexane to afford 0.46 g (47%) of azide as a white crystalline solid, melting point 100°-101° C.: 1H-NMR (CDCl3, Me4Si) 0.7-1.1 (t, J=6 Hz, CH2 --CH3), 1.1-1.7 (m), 1.75-2.1 (m), 4.6 (d, CH2 --N), 6.8-7.2(m,phenyl H), 7.3 (s,CH=N), 7.7 ppm (s,CH=N):

Workup

temperatureto warm to room temperature
additionAddition of ice
customthe precipitation of the product
filtrationFiltration
customgave 1.10 g of a crude product which
customwas carefully recrystallized from a 1 to 3 mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-b5221620f4454eeea7814d93748c37b4
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252594

Reaction notes

Loading…