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 2M hydrochloric acid (300 ml) until the solid dissolved to afford two clear phases. The (upper) organic phase was separated off and washed with 2M sodium hydroxide solution (300 ml), then dried (Na2SO4) and evaporated to a yellow solid. The solid was suspended in iso-hexane (10 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 2M sodium hydroxide 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-0eed5f6d87354085b3edf00316d5f7be

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132457B2