Formaldehyde → Methyl 3-(dimethylamino)-4-methoxybenzo[b]thiophene-2-carboxylate

HRID 2226871Notes

Reaction equation

HRID 2226871 reaction equation
NC1C2C(OC)=CC=CC=2SC=1[C:7](OC)=[O:8].C=O.Cl[C:20]1[C:28]2[C:27]([N:29]([CH3:31])[CH3:30])=[C:26]([C:32]([O:34][CH3:35])=[O:33])[S:25][C:24]=2[CH:23]=[CH:22][CH:21]=1>>[CH3:30][N:29]([CH3:31])[C:27]1[C:28]2[C:20]([O:8][CH3:7])=[CH:21][CH:22]=[CH:23][C:24]=2[S:25][C:26]=1[C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 10799875Methyl 3-amino-4-methoxy-1-benzothiophene-2-carboxylateHCID 18963790Methyl 4-chloro-3-(dimethylamino)benzo[b]thiophene-2-carboxylate

Product 1

HCID 18963783Methyl 3-(dimethylamino)-4-methoxybenzo[b]thiophene-2-carboxylate

Procedure

Alkylation of methyl 3-amino-4-methoxybenzo[b]thiophene-2-carboxylate (1.4 g, 5.9 mmol) [Beck J. R., supra] with paraformaldehyde as described for the preparation of methyl 4-chloro-3-(dimethylamino)benzo[b]thiophene-2-carboxylate provides methyl 3-(dimethylamino)-4-methoxybenzo[b]thiophene-2-carboxylate as a crude solid suitable for further synthesis; mp=69°-73° C.

Sources & evidence

ORD record
ord-78336d3907a5400098c6bbf2ec209efd
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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