1,2-Dichloroethane → N-(8-Phenyloctyl)-3-iodo-4-hydroxybenzamide

HRID 1743528Notes

Reaction equation

HRID 1743528 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:35]1([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C.O>[C:35]1([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][NH:49][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([I:1])[CH:3]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1455568-Phenyloctan-1-amineHCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)

Product 1

HCID 22237564N-(8-Phenyloctyl)-3-iodo-4-hydroxybenzamideYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 3-iodo-4-hydroxy-benzoic acid (2.64 g, 10.00 mmol) in fresh DMF (50 mL) at ambient temperature under an atmosphere of N2 was added EDC (2.11 g, 11.00 mmol), HOBt (1.49 g, 11.00 mmol) and DIPEA (1.94 g, 2.61 mL, 15.00 mmol). The solution was allowed to stir at ambient temperature for 1 hour at which time 8-phenyl-octylamine (2.46 g, 2.39 mL, 12 mmol) was added at one time. The solution was allowed to stir for an additional 4 hours at which time the it was diluted with water (250 mL) and extracted with ethyl acetate (250 mL). The organic phase was washed with water (2×250 mL), saturated aqueous NaHCO3 (250 mL) and saturated aqueous NaCl (250 mL). The solvent was removed in vacuo to yield 4.62 g of crude oil. The crude oil was purified by column chromatography (7:3 hexane:ethyl acetate) to yield 4.47 g (99%) of the desired product as a clear oil, which crystallized upon standing. 1H NMR (CDCl3) δ 8.19 (dd, 2H), 7.60 (dd, 1H), 7.20 (m, 4H), 6.97 (dd, 1H), 6.32 (t, 1H), 3.39 (q, 2H), 2.57 (t, 2H), 1.58 (m, 4H), 1.30 (m, 8H).

Workup

  1. additionwas added at one time
  2. extractionextracted with ethyl acetate (250 mL)
  3. washThe organic phase was washed with water (2×250 mL), saturated aqueous NaHCO3 (250 mL) and saturated aqueous NaCl (250 mL)
  4. customThe solvent was removed in vacuo
  5. customto yield 4.62 g of crude oil
  6. customThe crude oil was purified by column chromatography (7:3 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-3c15de0f2e394d6ab924ed31fd6d8a10
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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