3,4-Dimethoxybenzeneacetonitrile → HCID 11965335, compound

HRID 2366369Notes

Reaction equation

HRID 2366369 reaction equation
CN(C)CCNC.BrC1SC(C=O)=CC=1.[CH3:16][N:17]([CH3:29])[CH2:18][CH2:19][N:20]([CH3:28])[C:21]1[S:25][C:24]([CH:26]=O)=[CH:23][CH:22]=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:35][C:36]#[N:37]>>[CH3:30][O:31][C:32]1[CH:33]=[C:34](/[C:35](=[CH:26]/[C:24]2[S:25][C:21]([N:20]([CH2:19][CH2:18][N:17]([CH3:29])[CH3:16])[CH3:28])=[CH:22][CH:23]=2)/[C:36]#[N:37])[CH:38]=[CH:39][C:40]=1[O:41][CH3:42]

Participants

5

Reactant 4

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 784285-Bromothiophene-2-carbaldehydeHCID 64363844HCID 64363844, compound2×

Product 1

HCID 11965335HCID 11965335, compoundYield 32.3%

Procedure

Through the procedure as employed in Production step 1, an amine moiety derived from N,N,N′-trimethylethylenediamine (6.13 g) was introduced into 5-bromothiophene-2-carboxaldehyde (3.82 g), to thereby yield 5-[(2-dimethylamino-ethyl)-methyl-amino]-thiophene-2-carbaldehyde (yield: 3.26 g, 77%). The produced 5-[(2-dimethylamino-ethyl)-methyl-amino]-thiophene-2-carbaldehyde (2.12 g) was condensed with 3,4-dimethoxybenzyl cyanide (1.77 g) through Method A (production step 2), to thereby yield the target product (yield: 1.20 g, 32%).

Sources & evidence

ORD record
ord-35240c496b87445abafd6a9992c363a7
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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