Dimethylformamide → 2-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

2-Chloro-5-iodobenzoic acid (10.0 g) was suspended in dichloromethane (160 ml) then oxalyl chloride (4.0 ml) was added followed by N,N-dimethylformamide (40 μl). After 24 h the solvent was evaporated to afford a white solid, which was then redissolved in dichloromethane (160 ml). Triethylamine (14.8 ml) was added, followed by adamantane methylamine (6.9 ml) with cooling to keep the temperature below 30° C. The resulting slightly cloudy mixture was stirred for 1 h, then solvent was evaporated to give a pale yellow solid. The solid was stirred in a mixture of ethyl acetate (400 ml) and 2 M hydrochloric acid (300 ml) until the solid dissolved to afford two clear phases. The (upper) organic phase was separated off and washed with 2 M sodium hyroxide solution (300 ml), then dried (Na2SO4) and evaporated to a yellow solid. The solid was suspended in iso-hexane (100 ml), then filtered and washed with more iso-hexane (40 ml), and the resulting off-white solid dried in vacuo at 40° C. to afford the subtitled compound (14.0 g).

1. customAfter 24 h the solvent was evaporated
2. customto afford a white solid, which
3. temperaturewith cooling
4. customthe temperature below 30° C
5. customsolvent was evaporated
6. customto give a pale yellow solid
7. dissolutiondissolved
8. customto afford two clear phases
9. customThe (upper) organic phase was separated off
10. washwashed with 2 M sodium hyroxide solution (300 ml)
11. dry with materialdried (Na2SO4)
12. customevaporated to a yellow solid
13. filtrationfiltered
14. washwashed with more iso-hexane (40 ml)
15. customthe resulting off-white solid dried in vacuo at 40° C.

ORD record

ord-97e90492fd5e4fc89c78877891ea169a

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07297818B2