N-Hydroxyphthalimide → HCID 67542029, compound

HRID 389066Notes

Reaction equation

HRID 389066 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32][C:33]1[CH:34]=[CH:35][C:36]2[C:37]3[S:45][C:44]([CH2:46]O)=[N:43][C:38]=3[CH:39]=[N:40][C:41]=2[CH:42]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:32][C:33]1[CH:34]=[CH:35][C:36]2[C:37]3[S:45][C:44]([CH2:46][O:1][N:2]4[C:3](=[O:12])[C:4]5[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=5)[C:6]4=[O:7])=[N:43][C:38]=3[CH:39]=[N:40][C:41]=2[CH:42]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67542817HCID 67542817, compound

Product 1

HCID 67542029HCID 67542029, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Hydroxyphthalimide (4.15 g, 25.4 mmol) and triphenylphosphine (6.66 g, 25.4 mmol) were added to a suspension of (7-bromo[1,3]thiazolo[4,5-c]quinolin-2-yl)methanol (5.00 g, 16.9 mmol) in THF (170 mL). Diethyl azodicarboxylate (4.43 g, 25.4 mmol) was added dropwise, and the resulting solution was stirred at room temperature for 1.5 hours. A precipitate formed and was isolated by filtration, washed with THF, and dried in a vacuum oven to provide 5.59 g of 2-[(7-bromo[1,3]thiazolo[4,5-c]quinolin-2-yl)methoxy]-1H-isoindole-1,3(2H)-dione.

Workup

  1. customA precipitate formed
  2. customwas isolated by filtration
  3. washwashed with THF
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-aca0fe16027c4ff78defe805cf81a2f7
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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