Iodine → HCID 44248463, compound

HRID 1392661Notes

Reaction equation

HRID 1392661 reaction equation
[I:1]I.[C:3]1(=NN)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.C(N=C(N(C)C)N(C)C)(C)(C)C>CCOCC>[I:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]=1

Participants

5

Reactant 3

HCID 807IodineHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 4678681HCID 4678681, compound

Product 1

HCID 44248463HCID 44248463, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of I2 (14 g, 56 mmol) in ether (100 mL) added slowly at 5° C. over a 50 minute period to a solution of (3,4-dihydro-2H-naphthalen-1-ylidene)-hydrazine (4.5 g, 28 mmol, prepared from α-tetralone and hydrazine) and tert-butyl-tetramethylguanidine (43 g, 251 mmol, prepared from tetramethylurea, triphosgene, and tert-butylamine) in ether (100 mL). After the addition is complete, the mixture is stirred for 30 minutes and the ether (100 mL) is removed. The residue is heated for 1 hout at 90° C. and then cooled to room temperature. The mixture is diluted with ether and washed successively with 1N HCl, aq. Na2S2O3, aq. NaHCO3, and then saturated brine. The organic layers are dried, concentrated, and purified by flash chromatography (elution with hexane only) to give 6.4 g 4-iodo-1,2-dihydro-naphthalene: 1H NMR (CDCl3) 7.42 (d, 1H), 7.26-7.14 (m, 2H), 7.01 (d, 1H), 6.83 (t, 1H), 2.84 (t, 2H), 2.39-2.32 (m, 2H).

Workup

  1. additionAfter the addition
  2. customthe ether (100 mL) is removed
  3. temperaturecooled to room temperature
  4. additionThe mixture is diluted with ether
  5. washwashed successively with 1N HCl, aq. Na2S2O3, aq. NaHCO3
  6. customThe organic layers are dried
  7. concentrationconcentrated
  8. custompurified by flash chromatography (
  9. washelution with hexane only)

Sources & evidence

ORD record
ord-62bbf0036cfd41d497b18d1f5fae6677
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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