Diisopropylethylamine → 2,5-dimethyl-N-(3-ethoxycarbonyl-propionyl)-N-isopropyl-4-iodo-aniline

HRID 1017797Notes

Reaction equation

HRID 1017797 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([I:12])[C:9]([CH3:13])=[CH:8][C:3]=1[NH:4][CH:5]([CH3:7])[CH3:6].C(N(C(C)C)C(C)C)C.[Cl-].[C:24]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:25][CH2:26][C:27]([O-])=[O:28]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:11]=[C:10]([I:12])[C:9]([CH3:13])=[CH:8][C:3]=1[N:4]([C:27](=[O:28])[CH2:26][CH2:25][C:24]([O:31][CH2:32][CH3:33])=[O:30])[CH:5]([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 18404837Monoethyl succinate chlorideHCID 184052092,5-dimethyl-4-iodo-N-isopropyl-aniline

Product 1

HCID 184048522,5-dimethyl-N-(3-ethoxycarbonyl-propionyl)-N-isopropyl-4-iodo-aniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g (6.9 mmol) of 2,5-dimethyl-4-iodo-N-isopropyl-aniline and 2.4 ml of (13.8 mmol) of N-ethyl-diisopropylamine are dissolved in 30 ml of tetrahydrofuran and, after the addition of 1.5 ml (10.5 mmol) of ethyl succinate chloride, refluxed for 2 hours. After cooling to ambient temperature the mixture is diluted with ethyl acetate and washed successively with 1 molar hydrochloric acid and 1 molar sodium hydroxide solution. The organic phase is dried over sodium sulphate and evaporated down.

Workup

  1. temperaturerefluxed for 2 hours
  2. washwashed successively with 1 molar hydrochloric acid and 1 molar sodium hydroxide solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-16cdae9afe644568a4049ddbfca0cbce
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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