Dicyclohexylamine → HCID 53988638, compound

HRID 1057987Notes

Reaction equation

HRID 1057987 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:4]=1[O:5][CH2:6][C:7](Cl)=[O:8].COC1C=CC([N+]([O-])=O)=CC=1OCC(O)=O.S(Cl)(Cl)=O.[CH:37]1([NH:43][CH:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:44]1([N:43]([CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[C:7](=[O:8])[CH2:6][O:5][C:4]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:3]=2[O:2][CH3:1])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1

Participants

7

Reactant 5

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 15024720HCID 15024720, compoundHCID 54519412HCID 54519412, compound

Product 1

HCID 53988638HCID 53988638, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methoxy-5-nitro-phenoxyacetyl chloride (0.22 g, 0.9 mmol), prepared from 2-methoxy-5-nitro-phenoxyacetic acid (Brown et al., J. Chem. Soc. 1955, 3681) and thionyl chloride, in dichloromethane (10 mL) was added to a mixture of dicyclohexylamine (0.16 g, 0.9 mmol) and diisopropylethylamine (0.23 g, 1.76 mmol) in dichloromethane (20 mL), maintained at RT for 16 h, washed with water (2×20 mL), dried (Na2SO4), and concentrated in vacuo. The residue was recrystallized from methanol to afford the title compound (0.16 g).

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-c4eec0af195844de82a03ab5d0637475
Source dataset
uspto-grants-2003_02
Patent number
US06515027B1

Reaction notes

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