Acetic Acid → HCID 22414427, compound

HRID 1721322Notes

Reaction equation

HRID 1721322 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)[NH:10][CH3:11].[C:17](OCC)(OCC)(OCC)[CH2:18]C.[C:29](O)(=O)C>>[CH2:17]([C:11]1[N:10]([CH3:29])[CH:9]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1)[CH3:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 66995Ethyl orthopropionateHCID 22414364HCID 22414364, compound

Product 1

HCID 22414427HCID 22414427, compound

Procedure

A solution of 6.00 g of 2-amino-N-methyl-α-(3-thienyl)-benzeneethanamine and 10 ml of triethyl orthopropionate, was treated with 8 ml of glacial acetic acid. After refluxing for eight hours, the volatile components were removed at 70° C. on a rotary evaporator. The residual oil was decanted into an ice-water mixture and basified with 10% sodium hydroxide solution. The aqueous mixture was extracted with dichloromethane and the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated to provide 4,5-dihydro-2-ethyl-3-methyl-4-(3-thienyl)-3H-1,3-benzodiazepine as an oil.

Workup

  1. temperatureAfter refluxing for eight hours
  2. customthe volatile components were removed at 70° C. on a rotary evaporator
  3. customThe residual oil was decanted into an ice-water mixture
  4. extractionThe aqueous mixture was extracted with dichloromethane
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-577fa7e3b274471a89a8b9a8a0458851
Source dataset
uspto-grants-1996_04
Patent number
US05510346

Reaction notes

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