Dichloromethane → HCID 28492569, compound

HRID 1297753Notes

Reaction equation

HRID 1297753 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.[CH3:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br.C(Cl)Cl>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH3:34])[C:6](=[O:11])[C:5]2=[O:12]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 68895-BromoisatinHCID 6992o-Xylyl bromideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine

Product 1

HCID 28492569HCID 28492569, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 5-bromoisatin (90 mg, 0.4 mmol), 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polysteyrene (270-290 mg, 0.60-0.64 mmol, 2.2 mmol/g, Fluka) and 2-methylbenzyl bromide (0.054 mL, 0.4 mmol) in acetonitrile (4 mL) in a 20 dram scintillation vial and shake on a rotator for 2.5 days. Dilute with and a small amount of CH2Cl2 as needed to soluabilize solids. Filter off beads, washing with MeOH, and concentrate in vacuo. Triturate the resulting solid with diethyl ether (about 4 mL) and pipet off the liquid. Dry the solid to obtain approximately 70 mg of the title compound as crude material and use without further purification.

Workup

  1. filtrationFilter off beads
  2. washwashing with MeOH
  3. concentrationconcentrate in vacuo
  4. customTriturate the resulting solid with diethyl ether (about 4 mL) and pipet off the liquid
  5. customDry the solid

Sources & evidence

ORD record
ord-61bcf6830bd24818b80c74810c7137b1
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

Loading…