Hydroxyamine hydrochloride → HCID 58420951, compound

HRID 2178646Notes

Reaction equation

HRID 2178646 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][C:8]([CH:11]=O)=[CH:9][N:10]=1.Cl.[NH2:14]O>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][C:8]([C:11]#[N:14])=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 2356065554986-99-1

Product 1

HCID 58420951HCID 58420951, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.6 g 2-thiophen-2-yl-thiazole-5-carbaldehyde, 2.8 g hydroxylamine hydrochloride in 45 ml dimethylformamide are heated to 150° C. for 2 hours. The solvent is removed under reduced pressure. The crude product is purified by flash column chromatography in ethylacetate:hexane=1:5. 4.7 g of 2-thiophen-2-yl-thiazole-5-carbonitrile (11) are obtained. 1H (CDCl3): 8.2, 1H, d; 7.6, 1H, d; 7.5, 1H, d; 7.1, 1H, dd. 13C (CDCL3) 166.8 Cq, 152.5 Cq, 135.6 CH, 130.7 CH, 129.0 CH, 128.5 CH, 111.9 Cq 104.4 Cq.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe crude product is purified by flash column chromatography in ethylacetate

Sources & evidence

ORD record
ord-bd375fcecdd443b38aa3ef8f688fa3f6
Source dataset
uspto-grants-2015_06
Patent number
US09067942B2

Reaction notes

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