Methyl chloroformate → HCID 15654690, compound

HRID 1737888Notes

Reaction equation

HRID 1737888 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-a0ebb8ea602244b0acff9a06cf9b191b
Source dataset
uspto-grants-1999_10
Patent number
US05962491

Reaction notes

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