Methanol → HCID 20134489, compound

HRID 580674Notes

Reaction equation

HRID 580674 reaction equation
[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([CH:6]([Cl:13])[CH2:7][NH:8]C(C)(C)C)=[CH:4][C:3]=1[Cl:17].CO.Cl.[CH:21]([OH:24])(C)C>CCO>[ClH:13].[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([CH:6]([O:24][CH3:21])[CH2:7][NH2:8])=[CH:4][C:3]=1[Cl:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 13488797HCID 13488797, compoundHCID 21912024Isopropanol hydrochloride

Product 1

HCID 20134489HCID 20134489, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under N2 atmosphere, 11 g of 4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzyl chloride is added to 75 ml of methanol at 0° C. After 20 minutes, the cooling bath is removed and the reaction mixture is stirred at ambient temperature. After the reaction is completed, the mixture is evaporated to dryness in vacuo. The residue is stirred in 75 ml of H2O and the mixture is made alkaline with 6N NaOH solution and extracted with CH2Cl2 (3×50 ml). The organic phases are dried over MgSO4 and evaporated to dryness to afford an orange oil. This oil is dissolved in 150 ml of absolute EtOH and acidified with HCl/isopropyl alcohol solution to pH 2. The solution is evaporated to dryness and the residue is stirred in 75 ml of ethyl acetate. After cooling, this affords a pale yellow solid which is collected to give 6.97 g of the title compound, m.p. 195°-198° C. dec.

Workup

  1. customthe cooling bath is removed
  2. customthe mixture is evaporated to dryness in vacuo
  3. stirringThe residue is stirred in 75 ml of H2O
  4. extractionextracted with CH2Cl2 (3×50 ml)
  5. dry with materialThe organic phases are dried over MgSO4
  6. customevaporated to dryness
  7. customto afford an orange oil
  8. customThe solution is evaporated to dryness
  9. stirringthe residue is stirred in 75 ml of ethyl acetate
  10. temperatureAfter cooling
  11. customthis affords a pale yellow solid which
  12. customis collected

Sources & evidence

ORD record
ord-696a743b70d7442d82be8279bfb831c5
Source dataset
uspto-grants-1988_06
Patent number
US04754047

Reaction notes

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