1,1'-Carbonyldiimidazole → HCID 69471842, compound

Temperature

45 °C

To 4-bromo-2-chlorobenzoic acid (2.48 g) in pyridine (12 mL) and DMF (12 mL) was added CDI (1.88 g). The solution was stirred at 45° C. for 2 hours, cooled, treated with 2,3-diaminobenzamide dihydrochloride (2.36 g), stirred at ambient temperature for 18 hours, and concentrated. The concentrate was partitioned between ethyl acetate (70 mL) and water (100 mL) and filtered. The filtrant was washed with water and ethyl acetate and dried. This solid was suspended in acetic acid (40 mL) and the mixture was heated at 125° C. for 4 hours and filtered. The filtrate was cooled to ambient temperature and filtered. The filtrant was washed with methanol and dried to give the first batch of product. The mother liquor was concentrated and the concentrate was treated with dichloromethane and filtered to provide a second batch of solid.

1. temperaturecooled
2. stirringstirred at ambient temperature for 18 hours
3. concentrationconcentrated
4. customThe concentrate was partitioned between ethyl acetate (70 mL) and water (100 mL)
5. filtrationfiltered
6. washThe filtrant was washed with water and ethyl acetate
7. customdried
8. temperaturethe mixture was heated at 125° C. for 4 hours
9. filtrationfiltered
10. temperatureThe filtrate was cooled to ambient temperature
11. filtrationfiltered
12. washThe filtrant was washed with methanol
13. customdried
14. customto give the first batch of product
15. concentrationThe mother liquor was concentrated
16. additionthe concentrate was treated with dichloromethane
17. filtrationfiltered
18. customto provide a second batch of solid

ORD record

ord-c2f2d1d832114cb08d4acea1cb2e69b2

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697736B2