4-Chlorobenzaldehyde → HCID 69690017, compound

HRID 343071Notes

Reaction equation

HRID 343071 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:4][N:3]=1.CN(C)CCN(C)C.C([Li])CCC.[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=[O:42])=[CH:39][CH:38]=1>O1CCCC1.O>[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]([OH:42])[CH2:1][C:2]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:11][CH:12]=3)=[C:5]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:4][N:3]=2)=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 19608700HCID 19608700, compoundHCID 178418339Butyllithium

Product 1

HCID 69690017HCID 69690017, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a cold (-70° C.) solution of 4-[3-methyl-5-phenylisoxazol-4-yl]benzenesulfonamide (Example 13) (250 mg, 0.8 mmol) and tetramethylethylenediamine (277 mg, 2.4 mmol) in tetrahydrofuran (5 mL) under an argon atmosphere was added n-butyllithium (1.3 mL of 1.84M in hexane, 2.4 mmol). The solution was warmed to -40° C. for 15 minutes, recooled to -70° C., and a solution of 4-chlorobenzaldehyde (337 mg, 2.4 mmol) in tetrahydrofuran (3 mL) was added. The mixture was warmed to room temperature over 30 minutes, poured into water (25 mL) and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The crude product was chromatographed on silica gel using mixtures of acetone and hexane as eluents to give 165 mg of desired product as a crystalline solid: mp 165°-167° C. Anal. Calc'd. for C23H19ClN2O4S(454.93): C, 60.72; H, 4.21; N, 6.16; S, 7.05. Found: C, 60.33; H, 4.34; N, 5.87; S, 6.74.

Workup

  1. customrecooled to -70° C.
  2. temperatureThe mixture was warmed to room temperature over 30 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was chromatographed on silica gel using mixtures of acetone and hexane as eluents

Sources & evidence

ORD record
ord-95f1d5d22fd248cbae5028c465b4c74c
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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