Triethylamine → HCID 86603631, compound

HRID 226321Notes

Reaction equation

HRID 226321 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[S:21][CH:22]=[C:23](/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:24]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]2[CH2:14][CH2:15][CH:16]([NH:19][C:20]3[S:21][CH:22]=[C:23](/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:24]=3)[CH2:17][CH2:18]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 86603628HCID 86603628, compound

Product 1

HCID 86603631HCID 86603631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chlorobenzoyl chloride (0.19 mL) was added to a mixture of ethyl (2E)-3-[2-(4-piperidylamino)-1,3-thiazol-4-yl]acrylate dihydrochloride (0.5 g) and triethylamine (0.63 mL) in DMF (10 ml) under ice-cooling and the mixture was stirred at same temperature for 4.5 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and the mixture was extracted with an AcOEt. The extract layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give ethyl (2E)-3-(2-{[1-(4-chlorobenzoyl)-4-piperidyl]amino}-1,3-thiazol-4-yl)acrylate (0.48 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with an AcOEt
  3. washThe extract layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea3b6bb1b5214e7d8b34ef45858e2041
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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