Benzene, 1-chloro-3-isocyanato- → HCID 11702836, compound

HRID 564032Notes

Reaction equation

HRID 564032 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:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>C1COCC1>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH2:1][C:33]([NH:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=3)=[O:34])=[CH:3][C:4](=[O:14])[O:5]2)=[CH:10][CH:9]=1)#[N:13]

Participants

5

Reactant 3

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 2733832Lithium HexamethyldisilazideHCID 15015001HCID 15015001, compound

Product 1

HCID 11702836HCID 11702836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-2-oxo-2H-chromene-7-carbonitrile (673 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 3-chloro-1-isocyanato-benzene (222.3 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-(3-chloro-phenyl)-acetamide as a yellow solid.

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-13610d20569f4b299b4a42ac52745b3b
Source dataset
uspto-grants-2011_11
Patent number
US08067619B2

Reaction notes

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