Phthalimide → HCID 178444658, compound

HRID 2395167Notes

Reaction equation

HRID 2395167 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([SiH2:17][O:18][C:19]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:20]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:21]=1[S:22][C:23]1[C:24]([CH2:40]O)=[CH:25][CH:26]=[CH:27][C:28]=1[N:29]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH3:16])([CH3:15])[CH3:14].[C:54]1(=[O:64])[NH:58][C:57](=[O:59])[C:56]2=[CH:60][CH:61]=[CH:62][CH:63]=[C:55]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:13]([SiH2:17][O:18][C:19]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:20]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:21]=1[S:22][C:23]1[C:24]([CH2:40][N:58]3[C:54](=[O:64])[C:55]4[C:56](=[CH:60][CH:61]=[CH:62][CH:63]=4)[C:57]3=[O:59])=[CH:25][CH:26]=[CH:27][C:28]=1[N:29]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 137329066HCID 137329066, compound

Product 1

HCID 178444658HCID 178444658, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.68 ml (4.36 mmol) of diethyl azodicarboxylate was slowly added dropwise under argon and while cooling with ice to a solution of 1.95 g (3.35 mmol) of [6-(tert-butyl-diphenyl-silanyloxymethyl)-10-hexyl-phenothiazin-4-yl]-methanol, 876 mg (5.03 mmol) of phthalimide and 968 mg (3.69 mmol) of triphenylphosphine in 25 ml of tetrahydrofuran. The reaction mixture was stirred at 0° for 2 hours and at room temperature for 20 minutes and then worked up analogously to that described in Example 2.1.1 ea. The residue was chromatographed on 250 g of silica gel with diethyl ether/hexane (1:3), whereupon, after precipitation from hexane, 1.74 g (73.1%) of 2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-10-hexyl-phenothiazin-4-ylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione were obtained as a light yellowish amorphous solid. MS: 710 (M+, 100), 653(61), 506(16), 370(36), 308(41), 268(40), 224(21), 160(34), 130(45), 43(43).

Workup

  1. customThe residue was chromatographed on 250 g of silica gel with diethyl ether/hexane (1:3), whereupon
  2. customafter precipitation from hexane

Sources & evidence

ORD record
ord-95bcf63445e24d53984c0e04aa8f6cf6
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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