2-(Methylamino)ethanol → HCID 67226663, compound

HRID 2366366Notes

Reaction equation

HRID 2366366 reaction equation
CNCCO.BrC1SC(C=O)=CC=1.[OH:14][CH2:15][CH2:16][N:17]([CH3:25])[C:18]1[S:22][C:21]([CH:23]=O)=[CH:20][CH:19]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH2:31][C:32]#[N:33]>>[CH3:26][O:27][C:28]1[CH:29]=[C:30](/[C:31](=[CH:23]/[C:21]2[S:22][C:18]([N:17]([CH2:16][CH2:15][OH:14])[CH3:25])=[CH:19][CH:20]=2)/[C:32]#[N:33])[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]

Participants

5

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 667273,4-DimethoxybenzeneacetonitrileHCID 784285-Bromothiophene-2-carbaldehydeHCID 110631065-[(2-Hydroxyethyl)methylamino]-2-thiophenecarboxaldehyde2×

Product 1

HCID 67226663HCID 67226663, compoundYield 24%

Procedure

Through the procedure as employed in Production step 1, an amine moiety derived from N-methylethanolamine (2.25 g) was introduced into 5-bromothiophene-2-carboxaldehyde (1.91 g), to thereby yield 5-[(2-hydroxy-ethyl)-methyl-amino]-thiophene-2-carbaldehyde (yield: 991 mg, 53%). The produced 5-[(2-hydroxy-ethyl)-methyl-amino]-thiophene-2-carbaldehyde (682 mg) was condensed with 3,4-dimethoxybenzyl cyanide (654 mg) through Method A (production step 2), to thereby yield the target product (yield: 300 mg, 24%).

Sources & evidence

ORD record
ord-8a8de4671f6e47f3b81eae19784a3fef
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

Loading…