1-Naphthaleneacetic Acid → Methyl 4-methyl-2-(2-(naphthalen-1-yl)acetamido)thiophene-3-carboxylate

HRID 1519947Notes

Reaction equation

HRID 1519947 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[S:17][CH:18]=[C:19]([CH3:25])[C:20]=1[C:21]([O:23][CH3:24])=[O:22]>>[CH3:25][C:19]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:16]([NH:15][C:12](=[O:14])[CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[S:17][CH:18]=1

Participants

3

Reactant 2

HCID 68621-Naphthaleneacetic AcidHCID 2759773Methyl 2-amino-4-methylthiophene-3-carboxylate

Product 1

HCID 68756461Methyl 4-methyl-2-(2-(naphthalen-1-yl)acetamido)thiophene-3-carboxylate

Procedure

The title compound was prepared from 2-(naphthalen-1-yl)acetic acid (10 g, 54 mmol) and methyl 2-amino-4-methylthiophene-3-carboxylate (9.2 g, 54 mmol) according to protocol A (15.4 g, 85%) as a white solid. 1H NMR (CDCl3) δ 11.0 (s, 1H), 8.05-7.85 (m, 3H), 7.63-7.50 (m, 4H), 6.36 (s, 1H), 4.29 (s, 2H), 3.57 (s, 3H), 2.28 (s, 3H); 13C NMR (CDCl3) δ 168.3, 165.6, 149.3, 135.0, 134.0, 132.1, 129.8, 128.9, 128.6, 127.0, 126.2, 125.7, 123.7, 112.9, 112.2, 51.1, 41.9, 17.7; MH+ 340.

Sources & evidence

ORD record
ord-17e3d70e4ebe41c48c24947f1b009bdd
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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