Methyl chloroformate → HCID 15654690, compound

HRID 860931Notes

Reaction equation

HRID 860931 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, compound

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
  8. customto afford pale yellow needles (10.5 g. 90%), m.p. 113–115° C.

Sources & evidence

ORD record
ord-69c9dcf7f92f4b039cd99303d319e7ed
Source dataset
uspto-grants-2006_12
Patent number
US07153972B2

Reaction notes

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