2-Bromobutanal → 5-Ethyl-2-(4-methyl-2-nitro-phenyl)-thiazole

HRID 1445414Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Br[CH:15]([CH2:18][CH3:19])[CH:16]=O>>[CH2:18]([C:15]1[S:7][C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=2[N+:11]([O-:13])=[O:12])=[N:8][CH:16]=1)[CH3:19]

Participants

Reactant 2

HCID 126178112-Bromobutanal

HCID 541688084-Methyl-2-nitro-thiobenzamide

Product 1

HCID 576668255-Ethyl-2-(4-methyl-2-nitro-phenyl)-thiazoleYield 61%

Procedure

The procedure described in Example 15-1 was followed, except that 4-methyl-2-nitro-thiobenzamide (56) was used instead of 4-trifluoromethyl-2-nitro-thiobenzamide, and 2-bromo-butyraldehyde (54) was used instead of 1-bromo-3-methyl-butan-2-one, which gave the title compound (60 mg, 61%). LC/MS: (Method I): tR=1.52 min, >95%, m/z (ESI+)=249 (MH+).

Sources & evidence

ORD record: ord-fb586aba2aea4e328012fec6badf943d
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666834B2

Reaction notes

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