Water → HCID 86619810, compound

HRID 1713803Notes

Reaction equation

HRID 1713803 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[CH:8]1([C:14]2[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N1C=CC=CC=1.O>C(Cl)Cl>[CH:8]1([C:14]2[CH:15]=[CH:16][C:17]([NH:18][C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:19][CH:20]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 807644-Cyclohexylbenzenamine

Product 1

HCID 86619810HCID 86619810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloro(oxo)acetate (1.88 mL) was added to a stirred solution of 4-cyclohexylaniline (2980 mg) and pyridine (1.80 mL) in DCM (100 mL) at 0° C. After the addition was complete allowed to warm to ambient temperature and stirred for 16 hours. Water (50 mL) added. Extracted with DCM (2×75 mL). The organics were combined washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo to give methyl [(4-cyclohexylphenyl)amino](oxo)acetate (4133 mg) as a solid; 1H NMR δ 10.66 (1H, s), 7.60 (2H, d), 7.19 (2H, d), 3.84 (3H, s), 2.50 (1H+DMSO, m), 1.84-2.65 (5H, m), 1.46-1.14 (5H, m); MS m/e M−H− 260.

Workup

  1. additionAfter the addition
  2. extractionExtracted with DCM (2×75 mL)
  3. washThe organics were combined washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8fd35eb900e4d35a68c67cba9a7d9c4
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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