2-Bromo-1,1-dimethoxyethane → 2-(4-Methyl-2-nitro-phenyl)-thiazole

HRID 1445415Notes

Reaction equation

HRID 1445415 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.CO[CH:16](OC)[CH2:17]Br>C(O)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][CH:16]=[CH:17][N:8]=2)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 541688084-Methyl-2-nitro-thiobenzamide

Product 1

HCID 576667692-(4-Methyl-2-nitro-phenyl)-thiazoleYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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, bromoacetaldehyde-dimethylacetal was used instead of 1-bromo-3-methyl-butan-2-one, and the reaction was acid catalyst with 5% acetic acid. This gave the title compound (66 mg, 75%). LC/MS: (Method I): tR=0.98 min, >90%, m/z (ESI+)=221 (MH+).

Sources & evidence

ORD record
ord-2b53bb4c2ba54b45a189fb82db7a251d
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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