Water → HCID 59213237, compound

HRID 2062138Notes

Reaction equation

HRID 2062138 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH2:10])[CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:27])[C:19]1[C:20]([O:25][CH3:26])=[CH:21][CH:22]=[CH:23][CH:24]=1.O>C(Cl)Cl.CN(C1C=CC=CN=1)C.CCCCCC>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=1[NH:10][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])#[N:7]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 59213237HCID 59213237, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of 4-methyl-2-aminobenzonitrile (100 g, 0.75 mol) in 800 mL CH2Cl2 was added triethylamine (77.4 g, 0.76 mol) and dimethylaminopyridine (4.62 g, 0.037 mol). The solution was cooled to −5° C., and o-anisoyl chloride (129 g, 0.75 mol) was added over 1 h while maintaining the reaction temperature at 0-5° C. The reaction was then stirred at 30-40° C. for 3 h. Water (400 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated, and the aqueous solution was extracted with CH2Cl2 (600 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a solid residue, to which 800 mL hexane were added. The slurry was stirred and filtered to give N-(2-cyano-5-methyl-phenyl)-2-methoxy-benzamide as a yellow powder (180 g, 90%). mp 147-149° C. 1H NMR (CDCl3) δ 2.429 (s, 3H), 4.2 (s, 3H), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H); M/z (obs., [m+H]+)=268.

Workup

  1. temperaturewhile maintaining the reaction temperature at 0-5° C
  2. stirringthe mixture was stirred for 15 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous solution was extracted with CH2Cl2 (600 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a solid residue
  9. stirringThe slurry was stirred
  10. filtrationfiltered

Sources & evidence

ORD record
ord-e26da6c54c504a569f6f4bacfac73fdd
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

Loading…