Toluene → 1-Benzothiazol-6-yl-4-methyl-imidazolidin-2-one

HRID 80219

Reaction equation

HRID 80219 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][CH2:11][CH:12]([CH3:16])C(O)=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([N:19]([CH2:22]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])=CC=1.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl.CO>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:11][CH:12]([CH3:16])[NH:19][C:22]3=[O:31])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 687859923-(Benzothiazol-6-ylamino)-2-methyl-propionic Acid

Product 1

HCID 596362111-Benzothiazol-6-yl-4-methyl-imidazolidin-2-oneYield 71.42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

3-(Benzothiazol-6-ylamino)-2-methyl-propionic acid (I-167a: 500 mg, 2.118 mmol) was refluxed with triethylamine (1 mL, 6.989 mmol), DPPA (1.75 g, 6.35 mmol) and toluene (10 mL) at 120° C. in a sealed tube to afford the crude product. The reaction was monitored by TLC (5% methanol in chloroform). Purification by column chromatography on silica gel (2% methanol in chloroform) afforded 350 mg of the product (71.42% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-03c31806d2d749949be1a78dc18dd33b
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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