4-Iodo-o-toluidine → 4-Chloro-2-(1H-tetrazol-5-yl)-(4-iodo-2-methyl-phenyl)-amine

HRID 2297396Notes

Reaction equation

HRID 2297396 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Li+].CC([N-]C(C)C)C.[NH:18]1[C:22](C2C=C(Cl)C=CC=2F)=[N:21][N:20]=[N:19]1.C(Cl)[Cl:32].CO>C1COCC1>[Cl:32][C:7]1([I:9])[CH:6]=[CH:5][CH:3]([NH2:4])[C:2]([C:22]2[NH:21][N:20]=[N:19][N:18]=2)([CH3:1])[CH2:8]1

Participants

6

Reactant 4

HCID 832214-Iodo-o-toluidineHCID 2724682Lithium diisopropylamideHCID 21226129Dichloromethane methanolHCID 178505771HCID 178505771, compound

Product 1

HCID 1784216814-Chloro-2-(1H-tetrazol-5-yl)-(4-iodo-2-methyl-phenyl)-amineYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-methyl-4-iodoaniline (3.52 g, 0.0151 mol) in THF (25 mL) at −78° C., LDA (2 molar solution in THF, 11.33 mL, 0.02267 mol) was added dropwise. After stirring for 0.5 hours, a solution of 1-(tetrazol-5-yl)-2-fluoro-5-chlorobenzene (1.5 g, 0.00756 mol) in THF (15 mL) was added dropwise. The reaction was stirred for 16 hours as it warmed up to room temperature. The reaction mixture was quenched with aqueous conc. NH4Cl solution and extracted with CH2Cl2. The organic layer was dried (MgSO4) and the solvent removed giving a crude product as an oil. The oil with CH2Cl2->CH2Cl2:MeOH (9.7:0.3) gave 1.5 g (48%) of the desired product:

Workup

  1. stirringThe reaction was stirred for 16 hours as it
  2. customThe reaction mixture was quenched with aqueous conc. NH4Cl solution
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed
  6. customgiving a crude product as an oil

Sources & evidence

ORD record
ord-da98912b5b494a349bc0212971c5d6fe
Source dataset
uspto-grants-2002_12
Patent number
US06492363B2

Reaction notes

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