Phthalimide → 2-Phthalimidomethyl-3-methylimidazo[5,1-b]thiazole

HRID 1603440Notes

Reaction equation

HRID 1603440 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][C:15]1[S:19][C:18]2=[CH:20][N:21]=[CH:22][N:17]2[C:16]=1[CH3:23].[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:24]1(=[O:34])[N:28]([CH2:14][C:15]2[S:19][C:18]3=[CH:20][N:21]=[CH:22][N:17]3[C:16]=2[CH3:23])[C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19605134{3-Methylimidazo[4,3-b][1,3]thiazol-2-yl}methanol

Product 1

HCID 196050542-Phthalimidomethyl-3-methylimidazo[5,1-b]thiazoleYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere at room temperature, 0.705 ml of diethyl azodicarboxylate was added dropwise to 10 ml of an anhydrous tetrahydrofuran solution containing 505 mg of 2-hydroxymethyl-3-methylimidazo[5,1-b]thiazole, 662 mg of phthalimide and 1180 mg of triphenylphosphine, and the mixture was then stirred at room temperature for 4.5 hours. The solvent was evaporated under reduced pressure to obtain an oil, and this oil was then purified by a silica gel column chromatograph and successively Cephadex LH-20 to obtain 389.3 mg of 2-phthalimidomethyl-3-methylimidazo[5,1-b]thiazole as a lemon crystal.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto obtain an oil
  3. customthis oil was then purified by a silica gel column chromatograph and successively Cephadex LH-20

Sources & evidence

ORD record
ord-eab5fc04bd684cda8698c3aa00202a18
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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