Toluene → HCID 89553841, compound

HRID 590384Notes

Reaction equation

HRID 590384 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][CH2:13][OH:14])[C:5]#[N:6].C1(C)C=CC=CC=1.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.C(OCC)(=O)C>Cl.[Cl-].[Na+].O>[OH:14][CH2:13][CH2:12][CH2:11][N:10]1[C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[NH:1][C:23]1=[O:25]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 94429Triphosgene2×HCID 22349277HCID 22349277, compound2×

Product 1

HCID 89553841HCID 89553841, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

100 mg (0.52 mmol) of 3-amino-4-[(3-hydroxypropyl)amino]benzonitrile (Intermediate 12) are dissolved in 2.5 ml of 2N aqueous HCl and 1.5 ml of toluene are added. 150 mg (0.51 mmol) of triphosgene are added and the system is stirred at rt for 18 hr. After adding 75 additional mg of triphosgene and prosecuting the stirring for 1 hour 5 ml of brine and 25 ml of ethyl acetate are added and the system is stirred for 10 minutes. The organic layer is isolated and the aqueous one is extracted with 4×10 ml of ethyl acetate. The combined organic phases are washed with brine, dried and concentrated to give 106 mg (93% yield) of 100 pure (UPLC) title compound.

Workup

  1. customstirring for 1 hour
  2. additionare added
  3. stirringthe system is stirred for 10 minutes
  4. customThe organic layer is isolated
  5. extractionthe aqueous one is extracted with 4×10 ml of ethyl acetate
  6. washThe combined organic phases are washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-554081bd04d9463498eb14e1316cc2c8
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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