Sodium Carbonate → HCID 19867064, compound

HRID 1904376Notes

Reaction equation

HRID 1904376 reaction equation
[I:1]Cl.[CH3:3][C:4]1[CH:10]=[C:9]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)[CH:8]=[CH:7][C:5]=1[NH2:6].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[NH2:6][C:5]1[C:4]([CH3:3])=[CH:10][C:9]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[CH:8][C:7]=1[I:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24640Iodine chlorideHCID 14450263HCID 14450263, compound

Product 1

HCID 19867064HCID 19867064, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of iodine monochloride (4.46 g) in acetic acid (30 cm3) was added dropwise to a stirred solution of 2-methyl-4-(tetrazol-1-yl)aniline (4 g) in acetic acid (30 cm3). After 2 hours the mixture was brought to pH 6 by addition of aqueous sodium carbonate solution and extracted with dichloromethane (250 cm3). The organic phase was dried (MgSO4), filtered and evaporated to yield a dark brown solid. This solid was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane to afford 1-(4-amino-3-iodo-5-methylphenyl)tetrazole, m.p. 172°-175°, (6.2 g).

Workup

  1. extractionextracted with dichloromethane (250 cm3)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a dark brown solid
  6. customThis solid was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-b719c9407aa0416ea98c54f3746c72cc
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

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