4-Nitrobenzaldehyde → HCID 6610568, compound

HRID 1988354Notes

Reaction equation

HRID 1988354 reaction equation
Cl.[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].C([O-])(=O)C.[Na+].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)([O-:16])=[O:15]>O.C(O)C>[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[NH:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][S:5]2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 60960Cysteine HydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 6610568HCID 6610568, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3 g (17.08 mmoles) of L-Cysteine hydrochloride and 2.18 g (22.2 mmoles) of sodium acetate are dissolved in 75 ml of water. The solution is agitated vigorously during the addition by portions, of 3.10 g (20.5 mmoles) of 4-nitrobenzaldehyde in solution in 80 ml of 95% ethanol. A white precipitate rapidly appears in this pale yellow solution which forms abundantly. Agitation is maintained for one hour, the reaction mixture is then cooled down to 0° C. and filtered. The precipitate is successively rinsed with 200 ml of water, 100 ml of cold ethanol and 100 ml of ethyl ether. After drying a white powder is obtained with a yield of 87%. Melting point: 190-121° C.

Workup

  1. temperatureAgitation is maintained for one hour
  2. filtrationfiltered
  3. washThe precipitate is successively rinsed with 200 ml of water, 100 ml of cold ethanol and 100 ml of ethyl ether
  4. customAfter drying a white powder
  5. customis obtained with a yield of 87%

Sources & evidence

ORD record
ord-51d4a3e018d0444390c0f8cf733dfadf
Source dataset
uspto-grants-2009_06
Patent number
US07553976B2

Reaction notes

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