Water → HCID 67361482, compound

HRID 1951356Notes

Reaction equation

HRID 1951356 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][N:11]2[CH:14]=[C:15]([CH3:17])[N:16]=[C:10]2[C:9]=1[I:18].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].O>C(Cl)Cl>[I:18][C:9]1[C:10]2[N:11]([CH:14]=[C:15]([CH3:17])[N:16]=2)[CH:12]=[CH:13][C:8]=1[NH:7][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 49871062HCID 49871062, compound

Product 1

HCID 67361482HCID 67361482, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of sodium carbonate (0.57 g, 5.38 mmol) and amine 23 (1.47 g, 5.38 mmol) in 50 mL of dry CH2Cl2 was treated, under argon, over a period of 15 min with ethyl chloroformate (2.34 g, 22.6 mmol). The reaction mixture was stirred at room temperature for 24 h. Then, water (50 mL) was added and organic layer was recovered, the aqueous layer was extracted with additional CH2Cl2 (3×50 mL). The organic extracts were dried (Na2SO4), filtered and evaporated under vacuum. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford in order of elution: Compound 24 (820 mg, yield: 44%); mp 148° C.; IR (KBr) 3380, 3124, 3049, 2988, 1738, 1642, 1541; 1H NMR (400 MHz, DMSO-d6) δ 1.25 (t, 3H, J=7.1 Hz), 2.31 (s, 3H), 4.13 (q, 2H, J=7.1 Hz), 6.93 (d, 1H, J=7.1 Hz), 7.78 (s, 1H), 8.35 (d, 1H, J=7.1 Hz), 8.93 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 14.1, 14.5, 60.7, 81.8, 110.1, 111.5, 125.7, 137.2, 142.7, 144.5, 153.9. Anal. Calcd for C11H12IN3O2: C, 38.28; H, 3.50; N, 12.18. Found: C, 38.04; H, 3.55; N, 12.08.

Workup

  1. customorganic layer was recovered
  2. extractionthe aqueous layer was extracted with additional CH2Cl2 (3×50 mL)
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography
  7. customv/v) as eluent to afford in order of elution

Sources & evidence

ORD record
ord-0952068027284d0aa6ec010fae35fb89
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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