Chloroacetyl chloride → HCID 52952411, compound
Reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH2+:15][CH2:14][CH2:13]2)[O:9][N:8]=1.C(N(CC)CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl>[Cl:25][CH2:26][C:27]([N:15]1[CH2:16][CH2:17][CH:12]([C:10]2[O:9][N:8]=[C:7]([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)[N:11]=2)[CH2:13][CH2:14]1)=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
168 mg (1 eq.) of 4-(3-thiophen-2-yl[1,2,4]oxadiazol-5-yl)-piperidinium hydrochloride obtained in step 1) above and 220 μl (3.1 eq.) of triethylamine were dissolved in 1 ml of dichloromethane and stirred at a temperature of −15° C. A solution of chloroacetyl chloride (40 μl, 1 eq.) in 1 ml of dichloromethane (CH2Cl2) was added dropwise to the resulting suspension. The resulting mixture was stirred at room temperature for 2 hours. 20 ml of dichloromethane were then added, and the resulting organic phase was washed with three times 50 ml of 5% hydrochloric acid and then dried over MgSO4, filtered and evaporated. 2-Chloro-1-[4-(3-thiophen-2-yl[1,2,4]oxa-diazol-5-yl)piperid-1-yl]ethanone was obtained in the form of a white solid, in a yield of 95%.
Workup
- stirringThe resulting mixture was stirred at room temperature for 2 hours
- washthe resulting organic phase was washed with three times 50 ml of 5% hydrochloric acid
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-a1a484ab68cf4ab5858b809a13d501fb
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338599B2
Reaction notes
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