Ammonium Hydroxide → 5-Bromo-2-methyl-thiazole-4-carboxylic acid amide
Reaction equation
[Br:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([OH:10])=O.C1N=C[N:13](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>CN(C=O)C>[Br:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([NH2:13])=[O:10]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
5-Bromo-2-methyl-thiazole-4-carboxylic acid (14.4 g, 64.8 mmol) was dissolved in 100 ml DMF and CDI (11.6 g, 71.3 mmol) was added. The solution was stirred for 2 hrs at 60° C., cooled and NH4OH (150 ml, 973 mmol) was added. The reaction mixture was stirred over night at room temperature and extracted two times with ethyl acetate and water. The organic extracts were washed four times with water, dried with sodium sulfate, filtered and evaporated. The crude product (11.3 g, 79%) [MS: m/e=222.8 (M+H+)] was used without any further purification for the next step.
Workup
- temperaturecooled
- stirringThe reaction mixture was stirred over night at room temperature
- extractionextracted two times with ethyl acetate and water
- washThe organic extracts were washed four times with water
- dry with materialdried with sodium sulfate
- filtrationfiltered
- customevaporated
- customThe crude product (11.3 g, 79%) [MS: m/e=222.8 (M+H+)] was used without any further purification for the next step
Sources & evidence
- ORD record
- ord-bc0ec2d5171a4ebcb94a3a722b7cae87
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659401B2
Reaction notes
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