Dimethyl Sulfide → 3-(N-Methyamino)-2-carboethoxy-benzothiophene

HRID 235056Notes

Reaction equation

HRID 235056 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16](OC=O)(=O)C.CSC>>[CH3:16][NH:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 75269Acetic-formic anhydrideHCID 731510Ethyl 3-aminobenzo[b]thiophene-2-carboxylate

Product 1

HCID 133312793-(N-Methyamino)-2-carboethoxy-benzothiophene

Procedure

3-Amino-2-carboethoxy-benzothiophene (1.11 g, 5 mmol) was reacted with formic acetic anhydride followed by reduction by BH3.DMS, using the procedure described by Krishmanurthy in Tetrahedron Lett, 23:33 15-8 (1982), to yield 0.59 g of the title compound as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.39 (t, 3H), 3.41 (d, 3H), 4.33 (q, 2H), 7.28 (t, 1H), 7.41 (t, 1H), 7.53 (br s, 1H) (d, 1H), 8.18 (d, 1H).

Sources & evidence

ORD record
ord-ff5ff87923ba4f25aac4300e4b4b7532
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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