Hydrochloric Acid → HCID 53241495, compound

HRID 1505396Notes

Reaction equation

HRID 1505396 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C(C1C=CC(OC2N=CC(N[C:32]([C@H:34]([NH:37][C:38](=O)[O:39]C(C)(C)C)[CH2:35]C)=[O:33])=CC=2)=CC=1C(C)C)#N.Cl>ClCCl>[CH3:35][C@H:34]1[NH:37][C:38](=[O:39])[N:13]([C:12]2[CH:14]=[CH:15][C:9]([O:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:10][CH:11]=2)[C:32]1=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 151352Benzenamine, 4-(3-methylphenoxy)-HCID 68322480HCID 68322480, compound

Product 1

HCID 53241495HCID 53241495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To 4-[(3-methylphenyl)oxy]aniline (90 mg, 0.45 mmol) in dichloromethane (1 mL) was added with shaking at 35° C. an aliquot of approximately ⅓ of solution 1 slowly via syringe (over ca. 1 min). After 30 min, HCl (ca. 0.8 mL) was added and the heterogeneous mixture was heated at 100° C. for 2 hours with shaking, allowing the dichloromethane to distill off through a glass capillary. After cooling to room temperature the aqueous HCl was pipetted off and the residue dried under vacuum. The residue was purified by silica gel chromatography (Biotage instrument, 10 g column) eluting with 0-100% EtOAc/cHex to give after drying the title compound as a solid (30 mg).

Workup

  1. distillationto distill off through a glass capillary
  2. temperatureAfter cooling to room temperature the aqueous HCl
  3. customthe residue dried under vacuum
  4. customThe residue was purified by silica gel chromatography (Biotage instrument, 10 g column)
  5. washeluting with 0-100% EtOAc/cHex
  6. customto give
  7. dry with materialafter drying the title compound as a solid (30 mg)

Sources & evidence

ORD record
ord-942f6cf5e9e6499da6606b24f1b4f76c
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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