Water → HCID 59213237, compound

HRID 2406162Notes

Reaction equation

HRID 2406162 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
2.5 °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 0-5° 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) ppm; 13C NMR (CDCl3) δ 22.68, 55.7, 99, 111.27, 116.7, 120.3, 121.1, 124.15, 131.7, 132.25, 133.67, 141.32, 141.1, 157.2, 163. 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-e7675b8bb22548aa82c0f1dbc3a73e4b
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

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