p-Anisoyl chloride → HCID 24899449, compound

HRID 1819860Notes

Reaction equation

HRID 1819860 reaction equation
[CH2:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH2:4][CH2:3][CH:2]1[NH2:14].[C:15](Cl)(=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:2]2[CH:3]=[CH:4][C:5]3[O:6][C:7]4[CH2:13][CH2:12][CH2:11][CH2:10][C:8]=4[C:9]=3[CH:1]=2)=[O:24])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 21221605HCID 21221605, compound

Product 1

HCID 24899449HCID 24899449, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure of Example 1, tetrahydro-dibenzofuran-2-ylamine (0.94 g, 5.0 mmol), anisoyl chloride (0.91 g, 5.3 mmol), and triethylamine (2.1 mL, 15 mmol) in tetrahydrofuran (25 mL) provided 4-methoxy-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-benzamide (1.0 g). Mp 197.0-197.5° C.; Anal. Calcd. for C20H19NO3: C, 74.75; H, 5.96; N, 4.36; Found: C, 74.67; H, 5.87; N, 4.46.

Sources & evidence

ORD record
ord-df123cedec8944bb8e4c0ae1db5893e8
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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