Methyl chloroformate → HCID 15654690, compound

HRID 277467Notes

Reaction equation

HRID 277467 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:16][CH:15]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:29]([O:31][CH3:32])=[O:30]>N1C=CC=CC=1>[C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:3]2[C:2]([NH:1][C:29]([O:31][CH3:32])=[O:30])=[CH:11][CH:10]=[CH:9][C:4]=2[C:5]([O:7][CH3:8])=[O:6])=[CH:15][CH:16]=1)#[N:27]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 15654653Methyl 3-amino-2-{[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino}benzoate

Product 1

HCID 15654690HCID 15654690, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of methyl 3-amino-2-[(2′-cyanobiphenyl-4-yl)methylamino]benzoate (10 g) in pyridine (50 ml) was added dropwise methyl chloroformate (9.0 ml) under ice-cooling. The mixture was stirred at room temperature for 3 hours and concentrated. The residue was extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was recrystallized from ethyl acetate—hexane to afford pale yellow needles (10.5 g, 90%), m.p. 113-115° C.

Workup

  1. temperaturecooling
  2. concentrationconcentrated
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was recrystallized from ethyl acetate—hexane

Sources & evidence

ORD record
ord-3de6a647032f4e29b8bcc403f00701dd
Source dataset
uspto-grants-2002_03
Patent number
US06355808B2

Reaction notes

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