Acetyl chloride → HCID 86592020, compound

HRID 1349535Notes

Reaction equation

HRID 1349535 reaction equation
C(Cl)(=O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:13]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C@H:18]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:17][C@@H:16]2[CH3:32])=[O:14])[CH:10]=[CH:11][CH:12]=1.[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34]>CN(C=O)C>[CH2:33]([NH:35][C:36](=[O:37])[N:25]([C@H:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]([C:13](=[O:14])[C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[CH:8]=2)[C@@H:16]([CH3:32])[CH2:17]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8022Ethyl isocyanateHCID 1102969HCID 1102969, compound

Product 1

HCID 86592020HCID 86592020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(±)-Cis-3-ethyl-1-[1-(3-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-1-phenyl-urea was synthesized using general procedure A, substituting ethyl isocyanate for acetyl chloride using the following procedure. To a solution of (±)-cis-(3-methoxy-phenyl)-(2-methyl-4-anilino-3,4-dihydro-2H-quinolin-1-yl)-methanone in DMF was added ethyl isocyanate and reaction mixture was heated to 90° C. for 18 hours. The reaction was cooled to room temperature and concentrated. Crude mixture was purified by flash chromatography on silica gel using gradient elution hexane-ethyl acetate (5–20%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. customCrude mixture was purified by flash chromatography on silica gel using gradient elution hexane-ethyl acetate (5–20%)

Sources & evidence

ORD record
ord-22ac18aebf5e4bb8980f1e42ec9d7f6b
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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