Diethyl Ether → HCID 68687760, compound
Reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)C(C)C)(C)C.[I:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][C:26]=1[CH3:34].C(OCC)C>ClCCl>[I:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:30])=[CH:27][C:26]=1[CH3:34]Participants
Procedure
To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (9.38 g, 0.0509 mol) and N,N-diisopropylethylamine (13.31 mL, 0.0764 mol) in dry dichloromethane (250 mL) at 0° C. under nitrogen was added dropwise a solution of 4-iodo-3-methyl-benzoyl chloride (10.71 g, 0.0382 mol) in dry dichloromethane (30 mL) over ca. 10 minutes. The reaction mixture was allowed to warm slowly to room temperature with stirring over 3 hours then quenched by the addition of water (100 mL). The organic phase was separated, washed with 1 M hydrochloric acid (2×200 mL) and 5% wt/v aqueous sodium carbonate solution (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a cream solid. Diethyl ether (150 mL) was added and the resulting suspension stirred vigorously for 3 hours then filtered to afford the title compound (14.73 g, 90%) as a white solid, m.p. 152-153° C.
Workup
- customthen quenched by the addition of water (100 mL)
- customThe organic phase was separated
- washwashed with 1 M hydrochloric acid (2×200 mL) and 5% wt/v aqueous sodium carbonate solution (200 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customto afford a cream solid
- stirringthe resulting suspension stirred vigorously for 3 hours
- filtrationthen filtered
Sources & evidence
- ORD record
- ord-2591d841ab37416b9176f56a709f8bd6
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678787B2
Reaction notes
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