2-Methoxybenzoyl chloride → HCID 136105219, compound

HRID 1689987Notes

Reaction equation

HRID 1689987 reaction equation
NC1C=C(C)C2C(=CC3C(C=2)=CC=CC=3)C=1C#N.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[NH:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])#[N:20].C[O:40]C1C(C(Cl)=O)=CC=CC=1>N1C=CC=CC=1>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:29]1[NH:20][C:19](=[O:40])[C:21]2[C:22](=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[N:28]=1

Participants

4

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 131727983N-(2-Cyano-5-methyl-phenyl)-2-methoxy-benzamide 2-Amino-4-methyl anthronitrile

Product 1

HCID 136105219HCID 136105219, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

N-(2-Cyano-5-methyl-phenyl)-2-methoxy-benzamide 2-Amino-4-methyl anthronitrile (50.0 g, 378.3 mmol) was dissolved in 1 L dry pyridine and cooled to 0° C. O-Anisoyl chloride (63.0 ml, 453.96 mmol) was added dropwise over a 40 minute period and the reaction was allowed to warm to room temperature and stirred under a nitrogen atmosphere for 16 hours. The reaction was poured over 2 L of ice and the product formed a precipitate. The product was collected by vacuum filtration and dried for 3 days to produce the desired product a fluffy tan solid. Recovered 92.0 g 91% yield. LC/MS (10-99%) M/Z 267.2, retention time 3.34 minutes.

Workup

  1. temperatureto warm to room temperature
  2. customthe product formed a precipitate
  3. filtrationThe product was collected by vacuum filtration
  4. customdried for 3 days

Sources & evidence

ORD record
ord-6b6167e5e61347c29b5fc309903bedc8
Source dataset
uspto-grants-2012_04
Patent number
US08153642B2

Reaction notes

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