Acrylate → HCID 67550720, compound

HRID 1368991Notes

Reaction equation

HRID 1368991 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([CH:8]=O)=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13](=[O:18])[CH2:14][N:15]=[N+]=[N-])[CH3:11].[O-]CC.[NH4+].[Cl-].C([O-])(=O)C=C>O.CCOCC.C(O)C>[CH2:10]([O:12][C:13]([C:14]1[NH:15][C:5]2[CH:4]=[C:3]([S:2][CH3:1])[S:7][C:6]=2[CH:8]=1)=[O:18])[CH3:11]

Participants

9

Reactant 5

HCID 25188Acrylate2×HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 1194401-Hydroxyethyl radicalHCID 27369975-(Methylsulfanyl)thiophene-2-carbaldehyde

Product 1

HCID 67550720HCID 67550720, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

5-Methylsulfanyl-thiophene-2-carbaldehyde was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester added as ethanol solution (1 M of ester) to −20° C. ethoxide solution; allow to warm to 10° C. over 4 h; reaction poured into cold saturated aqueous NH4Cl; after ether extraction, acrylate organic phase washed with water until aqueous phase was neutral; crude acrylate solution heated at reflux for 2 h, allowed to cool to room temperature, stirred overnight).

Sources & evidence

ORD record
ord-6a8fb53050ad4e6e93b4324c7a15f7b6
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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