Sodium Carbonate → HCID 58625110, compound

HRID 1968827Notes

Reaction equation

HRID 1968827 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH:24]([O:27][CH3:28])[O:25][CH3:26])[CH:16]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>O.C1COCC1.C(Cl)Cl>[CH2:39]([O:38][C:36](=[O:37])[N:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH:24]([O:25][CH3:26])[O:27][CH3:28])[CH:16]=2)[CH:9]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate2×HCID 58625059HCID 58625059, compound

Product 1

HCID 58625110HCID 58625110, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of cyclohexyl-[3-(3-dimethoxymethyl-4-nitro-phenoxy)-phenyl]-amine (0.00868 mol) and Na2CO3 (0.02083 mol) in H2O (15 mL) and THF (75 mL) was stirred at 5° C. A solution of benzyl chloroformate (0.0104 mol) in THF (25 mL) was added dropwise over 15 min at 5° C. The resultant reaction mixture was stirred for 21 hours at room temperature. This mixture was extracted with diisopropyl ether. The separated organic layer was dried (MgSO4) and filtered, and the solvent was evaporated. The residue (0.00633 mol A) was reacted again with benzyl chloroformate (1.3 g, 0.0076 mol) and TEA (1.53 g, 0.0152 mol) in DCM (70 mL) under the same conditions as above. The residue was purified by column chromatography over silica gel (eluent: 95:5 CH2Cl2:hexane). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. customThe resultant reaction mixture
  2. stirringwas stirred for 21 hours at room temperature
  3. extractionThis mixture was extracted with diisopropyl ether
  4. dry with materialThe separated organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: 95:5 CH2Cl2:hexane)
  8. customThe product fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6b4eece35d9e474c9558cca8ee454d73
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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