2-Aminobenzyl alcohol → HCID 22120151, compound

HRID 1274074Notes

Reaction equation

HRID 1274074 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[S:10]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11]1>CC(O)C>[S:10]1[CH:14]=[CH:13][C:12]([CH:15]2[O:5][CH2:4][C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[NH:1]2)=[CH:11]1

Participants

4

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 22120151HCID 22120151, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-aminobenzyl alcohol (0.1218 mol), 3-thiophenecarboxaldehyde (0.1218 mol) and molecular sieves (3 Å) in 2-propanol (150 ml) was stirred overnight at room temperature. The crude reaction mixture was filtered, the residue was treated with CH2Cl2, and the mixture was filtered again. The solvent was evaporated, yielding 21.53 g (81%) of (±)-1,4-dihydro-2-(3-thienyl)-2H-3,1-benzoxazine (interm. 3).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. additionthe residue was treated with CH2Cl2
  4. filtrationthe mixture was filtered again
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ffdb43bd42eb4353827be728eb24d032
Source dataset
uspto-grants-2000_12
Patent number
US06156747

Reaction notes

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