Diethyl Ether → 2-Naphthalen-2-ylmethyl-1-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-isothiourea

HRID 895980Notes

Reaction equation

HRID 895980 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([NH2:20])=[S:19])=[CH:16][C:3]1=2.Br[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1.C(OCC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.O1CCCC1>[CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[CH2:22][S:19][C:18](=[NH:20])[NH:17][C:15]1[CH:14]=[CH:13][C:4]2[NH:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[NH:8][C:2](=[O:1])[C:3]=2[CH:16]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 703202-BromomethylnaphthaleneHCID 516892Sodium BicarbonateHCID 11300593(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

Product 1

HCID 1785118902-Naphthalen-2-ylmethyl-1-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-isothiourea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 50 mg, 0.18 mmol) in DMF (1 mL) was added 2-bromomethylnaphthalene (38.8 mg, 0.18 mmol) in one portion. The reaction mixture was stirred at room temperature for 1 hr then heated at 60° C. for 2 hrs. After this time, the solvent was removed in vacuo to leave an oily residue which was triturated with diethyl ether to give a yellow-brown solid. The solid was dissolved in 5 mL of tetrahydrofuran: 5 mL diethyl ether and treated with saturated sodium bicarbonate (10 mL). The organic layer was separated, dried over magnesium sulfate and evaporated to give a yellow oil. The product was purified by chromatography on silica gel (2% methanol: 98% dichloromethane). H1 NMR (acetone d6) δ: 8.81 (bs, 1H), 7.92-7.85 (m, 4H), 7.61 (bs, 1H), 7.50-7.39 (m, 4H), 7.09-6.91 (m, 7H), 5.81 (s, 2H).

Workup

  1. temperaturethen heated at 60° C. for 2 hrs
  2. customAfter this time, the solvent was removed in vacuo
  3. customto leave an oily residue which
  4. customwas triturated with diethyl ether
  5. customto give a yellow-brown solid
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give a yellow oil
  10. customThe product was purified by chromatography on silica gel (2% methanol: 98% dichloromethane)

Sources & evidence

ORD record
ord-cb656248c9fe4c25b2456862cfa809d8
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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