Imidazole → HCID 70637823, compound

HRID 435879Notes

Reaction equation

HRID 435879 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]O)=[CH:8][C:7]=1[N+:14]([O-:16])=[O:15].S(Cl)(Cl)=O.ClCC1C=CC(OCC2C=CC(Cl)=CC=2Cl)=C([N+]([O-])=O)C=1.[NH:47]1[CH:51]=[CH:50][N:49]=[CH:48]1.[H-].[Na+].S(=O)(=O)(O)O.N1C=CN=C1CC1C=CC(C2(Cl)C=CC(COCC3C=CC(Cl)(C4C=CC(CC5NC=CN=5)=CC=4[N+]([O-])=O)CC=3Cl)=C(Cl)C2)=C([N+]([O-])=O)C=1>CN(C)C=O.CCOCC>[NH:47]1[CH:51]=[CH:50][N:49]=[C:48]1[CH2:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C:3]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:2]=2[Cl:1])=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1

Participants

10

Reactant 7

HCID 795ImidazoleHCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 214816702,4-Dichloro-1-{[4-(chloromethyl)-2-nitrophenoxy]methyl}benzeneHCID 43319796{4-[(2,4-Dichlorophenyl)methoxy]-3-nitrophenyl}methanolHCID 86734464HCID 86734464, compound

Product 1

HCID 70637823HCID 70637823, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

5.5 g. of 4-hydroxy-3-nitrobenzaldehyde is reacted with 6.7 g. of 2,4-dichlorobenzyl chloride analogously to Chem. Abstr. 71 (1969) 30232, thus obtaining 5.2 g. of 4-(2,4-dichlorobenzyloxy)-3-nitrobenzaldehyde, m.p. 172°-174°. Of this product, 0.9 g. is dissolved in methanol/dioxane and reduced with 500 mg. of sodium borohydride, yielding 580 mg. of 4-(2,4-dichlorobenzyloxy)-3-nitrobenzyl alcohol, m.p. 126°-127°. 450 mg. of this product is heated with 5 ml. of thionyl chloride for 5 minutes to 100°. After the residual thionyl chloride has been removed under vacuum, the remainder is vacuum-filtered with ethanol, thus producing 400 mg. of (4-chloromethyl-2-nitrophenyl)-(2,4-dichlorobenzyl)-ether, m.p. 147°-149°. 300 mg. of this ether is added to a solution of 68 mg. of imidazole in 3 ml. of dimethylformamide, which was agitated with the addition of 30 mg. of sodium hydride suspension (80%) for 1 hour at room temperature, and the mixture is stirred for another hour at room temperature. Then, the mixture is combined with 1N sulfuric acid and the thus-precipitated product is vacuum-filtered, dissolved in methanol/chloroform, and extracted with 1N sodium hydroxide solution. The chloroform phase is washed with water, dried, and evaporated. Recrystallization from cyclohexane/benzene yields 260 mg. of [4-(4-(1-imidazolylmethyl)-2-nitrophenyl]-(2,4-dichlorobenzyl)-ether, m.p. 120°-124°.

Workup

  1. temperatureof this product is heated with 5 ml
  2. customAfter the residual thionyl chloride has been removed under vacuum
  3. filtrationthe remainder is vacuum-filtered with ethanol
  4. customthus producing 400 mg
  5. filtrationthe thus-precipitated product is vacuum-filtered
  6. dissolutiondissolved in methanol/chloroform
  7. extractionextracted with 1N sodium hydroxide solution
  8. washThe chloroform phase is washed with water
  9. customdried
  10. customevaporated
  11. customRecrystallization from cyclohexane/benzene
  12. customyields 260 mg

Sources & evidence

ORD record
ord-76953dde1dd743e7a454f4a07e2b9acb
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Reaction notes

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