Chlorophenyl isocyanate → HCID 86610811, compound

HRID 564033Notes

Reaction equation

HRID 564033 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]=[C:33]=[O:34]>C1COCC1>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH2:1][C:33]([NH:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[Cl:25])=[O:34])=[CH:3][C:4](=[O:14])[O:5]2)=[CH:10][CH:9]=1)#[N:13]

Participants

5

Reactant 3

HCID 76833Chlorophenyl isocyanateHCID 2733832Lithium HexamethyldisilazideHCID 15015001HCID 15015001, compound

Product 1

HCID 86610811HCID 86610811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-2-oxo-2H-chromene-7-carbonitrile (670 mg, 3.6 mmol) in dry THF (30 mL) at −20° C. was added drop wise 1.0 M LiHMDS solution in THF (5.4 mL). After 30 minutes 2-chloro-1-isocyanato-benzene (221 mg) was added into the reaction mixture and the reaction mixture was stirred for 1 hour. The reaction mixture was then quenched with saturated aqueous ammonium chloride (25 mL) and extracted with ethyl acetate (50 mL). The organic layer was separated and dried over sodium sulfate, then concentrated and purified on silica gel eluted with 30%-100% ethyl acetate in hexanes to yield 2-(7-cyano-2-oxo-2H-chromen-4-yl)-N-(2-chloro-phenyl)-acetamide as a foam.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride (25 mL)
  2. extractionextracted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified on silica gel
  7. washeluted with 30%-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-90d78da3532e421583130e4bcb0c8c26
Source dataset
uspto-grants-2011_11
Patent number
US08067619B2

Reaction notes

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