Phthalimide → HCID 69412703, compound

HRID 349163Notes

Reaction equation

HRID 349163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH2:21]O)[CH:18]=[CH:19][CH:20]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH2:21][N:46]4[C:45](=[O:47])[C:44]5=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]5[C:42]4=[O:52])[CH:18]=[CH:19][CH:20]=3)[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69413563HCID 69413563, compound2×

Product 1

HCID 69412703HCID 69412703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The phenylmethylalcohol compound (1.98 grams) (Scheme C, Compound C1) was dissolved in tetrahydrofuran (100 mL). Triphenylphosphine (1.84 grams), phthalimide (1.03 grams) and diethylazodicarboxylate (1.10 mL) were added to the mixture which was then stirred for 16 hours before being evaporated in vacuo. The residue was column chromatographed (silica gel) using a mobile phase of hexane-ethyl acetate 2:1 to give a N-[3-[[4-(4-chlorophenyl)-2-thiazolyl]methoxy]phenylmethyl]phthalimide (Scheme C, Compound C2). Mp 156.5–157.5° C.; MS 461 (MH+).

Workup

  1. custombefore being evaporated in vacuo
  2. customchromatographed (silica gel)

Sources & evidence

ORD record
ord-6cad1b2aa9b34e7da1cceb21a86b45c4
Source dataset
uspto-grants-2007_02
Patent number
US07179808B2

Reaction notes

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