Water → HCID 178486071, compound

HRID 2380663Notes

Reaction equation

HRID 2380663 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:11][C:10]([C:20](=[N:32][OH:33])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:34][N:35]=[C:36]=[O:37].C(N(CC)CC)C.O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[CH2:11][C:10]([C:20](=[N:32][O:33][C:36]([NH:35][CH3:34])=[O:37])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 178526358HCID 178526358, compound

Product 1

HCID 178486071HCID 178486071, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.75 g (0.0015 mol) of the product obtained from Example 4 dissolved in 15 mL tetrahydrofuran was added 0.097 g (0.0017 mol) of methyl isocyanate and 0.20 g (0.002 mol) of triethylamine. The reaction mixture was stirred at room temperature for 18 hours, poured into cold water (50 mL) and extracted with ethyl acetate (3×50 mL). The ethyl acetate layer was washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 0.44 g of a white solid, mp 75° C. to 77° C.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe ethyl acetate layer was washed with brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7deed55f9a514ae8967f3ecc56e9ef3b
Source dataset
uspto-grants-1994_11
Patent number
US05369121

Reaction notes

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