Acetic Acid → HCID 59770502, compound

HRID 2218660Notes

Reaction equation

HRID 2218660 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:23])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(O)=O.[O-:28][C:29]#[N:30].[Na+]>O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH:23][C:29]([NH2:30])=[O:28])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517096Sodium CyanateHCID 59770309HCID 59770309, compound

Product 1

HCID 59770502HCID 59770502, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

According to the procedure of F. Kurzer, Org. Syn. Coll. Vol (IV) 49 (1963), mix 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenylamine ((133 mg, 0.54 mmol) with HOAc (4 mL) and water (2 mL). Dissolve sodium cyanate (80 mg, 1.2 mmol) in water (1 mL) and add this solution to the amine derivative. Stir the reaction at room temperature for 2 h. and then pour into water (100 mL). Extract the title compound into EtOAc, dry (MgSO4) and concentrate to give 240 mg crude product. Purify on silica gel using EtOAc/hexane to give 150 mg (48%) product as a colorless oil. MS (ES) 341 (M+1), 339 (M−1). HPLC shows 96.6% purity.

Workup

  1. customthe reaction at room temperature for 2 h.
  2. extractionExtract the title compound into EtOAc
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate
  5. customto give 240 mg crude product
  6. customPurify on silica gel

Sources & evidence

ORD record
ord-32e712da9354462a87e7a23cdb6b20e1
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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