Phthalimide → HCID 70077822, compound

HRID 2395112Notes

Reaction equation

HRID 2395112 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Si:13]([O:20][CH2:21][C:22]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:23]=1[S:24][C:25]1[C:26]([CH2:37]O)=[CH:27][CH:28]=[CH:29][C:30]=1[N:31]2[CH3:36])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Si:13]([O:20][CH2:21][C:22]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:23]=1[S:24][C:25]1[C:26]([CH2:37][N:43]3[C:39](=[O:49])[C:40]4[C:41](=[CH:45][CH:46]=[CH:47][CH:48]=4)[C:42]3=[O:44])=[CH:27][CH:28]=[CH:29][C:30]=1[N:31]2[CH3:36])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22075659HCID 22075659, compound

Product 1

HCID 70077822HCID 70077822, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.62 ml (10.34 mmol) of diethyl azodicarboxylate were slowly added dropwise while cooling with ice and under argon to a solution of 3.09 g (7.97 mmol) of [6-(tert-butyl-dimethylsilanyloxymethyl)-10-methyl-phenothiazin-4-yl]-methanol, 1.76 g (11.9 mmol) of phthalimide and 2.30 g (8.75 mmol) of triphenylphosphine in 65 ml of tetrahydrofuran. The reaction mixture was stirred at 0° for 3 hours and then worked-up analogously to that described in Example 2.1.1.ea. The residue was chromatographed on 500 g of silica gel with toluene/ethyl acetate (19:1), whereupon, after crystallization from ethanol/ethyl acetate, 3.22 g (78.2%) of 2-[6-(tert-butyl-dimethylsilanyloxymethyl)-10-methyl-phenothiazin-4-ylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione were obtained as a light yellow solid of m.p. 195°-196°.

Workup

  1. customThe residue was chromatographed on 500 g of silica gel with toluene/ethyl acetate (19:1), whereupon
  2. customafter crystallization from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-1515d7d905db43bc9b9040df8bf63aee
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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