4-Nitrobenzaldehyde → HCID 21915117, compound

HRID 2117882Notes

Reaction equation

HRID 2117882 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([CH2:10]Cl)[N:9]=1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].[N+:42]([C:45]1[CH:52]=[CH:51][C:48]([CH:49]=O)=[CH:47][CH:46]=1)([O-:44])=[O:43]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8](/[CH:10]=[CH:49]/[C:48]2[CH:51]=[CH:52][C:45]([N+:42]([O-:44])=[O:43])=[CH:46][CH:47]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 11776TriphenylphosphineHCID 12308581ethyl 2-(acetylamino)-4-(chloromethyl)-1,3-thiazole-5-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21915117HCID 21915117, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of ethyl 2-(acetylamino)-4-(chloromethyl)-1,3-thiazole-5-carboxylate (1.0 g, 3.81 mmol) in N,N-dimethylformamide (20 mL) was added triphenylphosphine (1.2 g, 4.57 mmol) at room temperature. The resultant mixture was stirred at 65° C. for 5 hours. To the mixture was added potassium tert-butoxide (555 mg, 4.95 mmol) at 5° C., and the resultant mixture was stirred at 5° C. for 30 minutes p-Nitrobenzaldehyde (805 mg, 5.33 mmol) was added at 5° C. After stirring for 1 hour at room temperature, the reaction was quenched with water, and the mixture was filtered to give the title compound (1.0 g, 72.7%) as a yellow solid.

Workup

  1. additionwas added at 5° C
  2. customthe reaction was quenched with water
  3. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-d4acf51e381e4d7e8c4dce6c75572fa8
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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