Benzaldehyde → HCID 20475695, compound

HRID 905244Notes

Reaction equation

HRID 905244 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][C:7]([S:10]([CH2:13]P(OCC)(=O)OCC)(=[O:12])=[O:11])=[N:8][CH:9]=1.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>C1C=CC=CC=1>[CH:13](/[S:10]([C:7]1[N:8]=[CH:9][C:4]([Cl:3])=[CH:5][N:6]=1)(=[O:11])=[O:12])=[CH:22]\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 54057565HCID 54057565, compound

Product 1

HCID 20475695HCID 20475695, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

Sodium hydride dispersion (55-60%, 2 mmol) was further dispersed in benzene (4 ml) and added gradually to a solution of diethyl (5-chloropyrimidin-2-sulfonyl)methanephosphonate (0.66 g, 2 mmol) in benzene (4 ml). The mixture was stirred for 10 min before a solution of benzaldehyde (0.21 g, 2 mmol) in benzene (2 ml) was added. The resultant mixture was stirred at room temperature overnight before extraction with water. Evaporation of the dried (MgSO4) benzene solution left the product which was recrystallised from ethanol; yield 0.20 g 35%, m.p. 150° C. 1H NMR (CDCl3): δ7.24 and 7.90 (2H-vinyl, Jvic 16 Hz), 7.60 (Ph, m.), 8.90 (2H-4,6).

Workup

  1. additionwas added
  2. customEvaporation of the
  3. dry with materialdried (MgSO4) benzene solution
  4. waitleft the product which
  5. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-41b89d508c264a3081fcd6a97f634d60
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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