Dibutylamine → (E)-2-[2-(4-Dibutylaminopropoxyphenyl)ethenyl]-6-methoxybenzoxazole

HRID 1723512Notes

Reaction equation

HRID 1723512 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].Cl[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[O:24][C:25]3[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:17][CH:16]=1>>[CH2:1]([N:5]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18](/[CH:21]=[CH:22]/[C:23]2[O:24][C:25]3[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:19][CH:20]=1)[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 8148DibutylamineHCID 14146345(E)-2-[2-(4-chloropropoxyphenyl)ethenyl]-6-methoxybenzoxazole

Product 1

HCID 14146351(E)-2-[2-(4-Dibutylaminopropoxyphenyl)ethenyl]-6-methoxybenzoxazoleYield 8%

Procedure

Reaction of this product (2.4 g, 6.9 mmol) with dibutylamine produced 0.20 g (8% yield) of the named compound as the HCl salt, mp 151°-152° C. IR(KBr): 1600 cm-1. MS: 437(MH+). 1H NMR (CDCl3): δ 8.31-6.91 (m, 9H), 4.18 (t, J=5.1 Hz, 2H), 3.91 (s, 3H), 3.09 (m, 4H), 2.67-0.82 (m, 18H).

Sources & evidence

ORD record
ord-36f11ddb59fd4d60b1a03a494497700a
Source dataset
uspto-grants-1989_08
Patent number
US04861897

Reaction notes

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