Triethylamine → N-[4-methoxy-3-(naphthylmethoxy)phenyl]naphthylformamide

HRID 431396Notes

Reaction equation

HRID 431396 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)C=1.[C:23]1(C(Cl)=O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C[C:44](N(C)C)=[O:45]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:28]2[C:27]3[C:32](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:31]=[CH:30][CH:29]=2)[CH:44]=[O:45])=[CH:5][C:4]=1[O:10][CH2:11][C:12]1[C:19]2[C:20](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:21]=[CH:22][CH:13]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 701461-Naphthalenecarbonyl chlorideHCID 699120564-Methoxy-3-(2-naphthylethoxy)phenylamine

Product 1

HCID 86586381N-[4-methoxy-3-(naphthylmethoxy)phenyl]naphthylformamide

Procedure

N-[4-methoxy-3-(naphthylmethoxy)phenyl]naphthylformamide (Exemplary Compound 47) was prepared using the same experimental conditions used to prepare Exemplary Compound 52 (Scheme X, above). From 4-methoxy-3-(2-naphthylethoxy)phenylamine (350 mg, 1.25 mmol) and 1-naphthoyl chloride (240 mg, 1.25 mmol) in 10 mL of dimethyl acetamide containing triethylamine (1 mL, 7.17 mmol) stirred at room temperature for 16 h., was obtained 280 mg of product in (52%) yield as white needles after recrystallization from ethyl acetate/hexane: mp 161-163° C. 1H NMR (400 MHz, Me2SO-d6) δ3.74 (s, 3H); 5.52 (s, 2H); 7.01 (d, 1H, J=8.8); 7.43 (dd, 1H, J=2.3, 8.7); 7.51-7.74 (m, 9H); 7.94-8.21 (m, 6H); 10.43 (s, 1H). Anal. Calcd for C29H23NO3: C, 80.35; H, 5.35; N, 3.23. Found: C, 80.25; H, 5.39; N, 3.19.

Sources & evidence

ORD record
ord-579f6240b6be4bfebfacda1235e61edb
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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