Chlorotrimethylsilane → HCID 54681348, compound

HRID 2394031Notes

Reaction equation

HRID 2394031 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li].C[Si]([NH-])(C)C.Cl[Si](C)(C)C.[C:22]1([CH2:28][CH2:29][S:30][CH:31]([C:35]([OH:37])=O)[C:32]([OH:34])=[O:33])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[K+].[Br-]>O>[OH:37][C:35]1[CH:29]=[C:28]([C:22]2[CH:27]=[CH:26][C:25]([NH:10][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:24][CH:23]=2)[O:34][C:32](=[O:33])[C:31]=1[S:30][CH2:29][CH2:28][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 7370BenzenesulfonamideHCID 253877Potassium BromideHCID 3028194LithiumHCID 19596072[(Phenylethyl)thio]propanedioic acidHCID 53627528(Trimethylsilyl)amide

Product 1

HCID 54681348HCID 54681348, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared by Method A using the corresponding benzenesulfonamide (3.0 g, 10.91 mmol), lithium bis(trimethylsilylamide (3.65 g, 21.82 mmol), chlorotrimethylsilane (3.68 mL, 21.82 mmol) and diethyl ester of [(phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). m.p. 89°-91° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.78 (t, 2 H), 3.03 (t, 2 H), 6.86 (s, 1 H), 7.25 (m, 6 H), 7.72 (t, 3 H), 7.86 (m, 5 H); IR (KBr) 3443, 3335, 1725, 1632, 1543, 1383, 1171, 912, 729, 581, 552 cm-1 ; Analysis calc'd for C25H21N1S2O5.H2O: C, 60.35; H, 4.66; N, 2.81; found: C, 60.13; H, 4.47; N, 3.23.

Sources & evidence

ORD record
ord-04ad8d2468584e6481c028545fd5f5c6
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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