Phthalimide → HCID 178479877, compound

HRID 2395160Notes

Reaction equation

HRID 2395160 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([SiH2:17][O:18][C:19]([CH3:38])([CH3:37])[C:20]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:21]=1[S:22][C:23]1[C:24]([CH2:35]O)=[CH:25][CH:26]=[CH:27][C:28]=1[N:29]2[CH3:34])([CH3:16])([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>[C:13]([SiH2:17][O:18][C:19]([CH3:38])([CH3:37])[C:20]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:21]=1[S:22][C:23]1[C:24]([CH2:35][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:25][CH:26]=[CH:27][C:28]=1[N:29]2[CH3:34])([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 137329064HCID 137329064, compound

Product 1

HCID 178479877HCID 178479877, 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-dimethyl-silanyloxymethyl)-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-dimethyl-silanyloxymethyl)-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-03bd2ff2b7734958a35962f6863c84bf
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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