Benzyl Bromide → HCID 87546111, compound

HRID 1435693Notes

Reaction equation

HRID 1435693 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:22])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][OH:21])[N:18]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.C(Cl)Cl.CC(C)=O>[CH2:23]([O:21][CH2:20][CH2:19][C:17]1[N:18]=[C:14]([NH:13][S:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[C:5]=2[CH3:22])(=[O:11])=[O:12])[S:15][CH:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 87545745HCID 87545745, compound

Product 1

HCID 87546111HCID 87546111, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (95% dry, 76 mg, 3.00 mmol) was added to a stirred solution of EXAMPLE 181A (400 mg, 1.20 mmol) in THF (10 mL) at room temperature. After stirring for 15 min. the mixture was treated with benzyl bromide (226 mg, 1.32 mmol). After 2 h at 50° C. additional sodium hydride (60 mg, 2.40 mmol) and benzyl bromide (142 mg, 1.20 mmol) were added in two equal portions under a period of 2 h. The reaction was quenched by adding 1M HCl (3 mL) at room temperature. The mixture was extracted with DCM and dried (Sodium sulfate). Evaporation of the solvent gave a residue which was purified by flash chromatography on silica gel eluting with 5% acetone in DCM giving (105 mg, 0.25 mmol, 21%) which solidified on standing: MS (Ionspray, [M+H]+) m/z 322. Anal. Calcd. (found) for C19H19ClN2O3S2.0.5 CH2Cl2: C, 50.3 (50.7)%; H, 4.3 (4.1)%; N, 6.0 (5.9)%.

Workup

  1. customThe reaction was quenched
  2. additionby adding 1M HCl (3 mL) at room temperature
  3. extractionThe mixture was extracted with DCM
  4. dry with materialdried (Sodium sulfate)
  5. customEvaporation of the solvent
  6. customgave a residue which

Sources & evidence

ORD record
ord-69039ee9523e4bc8bd78de4b31e2be10
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

Loading…