Chlorosuccinimide → HCID 16731659, compound

HRID 844150Notes

Reaction equation

HRID 844150 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=2[NH2:18])=[N:6][CH:7]=1.[Cl:20]N1C(=O)CCC1=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[C:14]([Cl:20])[CH:13]=[C:12]([O:16][CH3:17])[C:11]=2[NH2:18])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 16733151HCID 16733151, compound

Product 1

HCID 16731659HCID 16731659, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
52.5 °C

Procedure

To N-(5-chloropyridin-2-yl)-2-amino-3-methoxybenzamide (39 g, 140 mmol) in benzene (2 L) was added N-chlorosuccinimide (20 g, 148 mmol) and the reaction heated at 50-55° C. After 24 hours the reaction was cooled to ambient temperature and concentrated of all volatiles in vacuo. The resulting solid was dissolved in ethyl acetate (1 L), washed with water (3×100 mL), dried over sodium sulfate, and concentrated. Recrystallization from benzene afforded 40 g (90% yield) of N-(5-chloropyridin-2-yl)-2-amino-3-methoxy-5-chlorobenzamide as off-white needles; NMR (CDCl3) 8.6 (br, 1), 8.3 (m, 2), 7.7 (dd, 1), 7.1 (d, 1), 6.8 (d, 1), 5.9 (br, 1), 3.9 (s, 3) ppm.

Workup

  1. temperatureAfter 24 hours the reaction was cooled to ambient temperature
  2. concentrationconcentrated of all volatiles in vacuo
  3. dissolutionThe resulting solid was dissolved in ethyl acetate (1 L)
  4. washwashed with water (3×100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customRecrystallization from benzene

Sources & evidence

ORD record
ord-c663cafc80bb4f31814789b6206746b3
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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