Diisopropylethylamine → HCID 90313013, compound

HRID 1523749Notes

Reaction equation

HRID 1523749 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].CCN(C(C)C)C(C)C.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25]>C(#N)C>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 6410003-Amino-3-methylbutan-1-ol

Product 1

HCID 90313013HCID 90313013, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 20 mL vial were added a stirbar, 3-amino-3-methylbutan-1-ol (428 mg, 4.15 mmol), ACN (5 mL), and DIPEA (2.0 mL, 12 mmol). The mixture was then treated with 2-bromobenzene-1-sulfonyl chloride (994 mg, 3.89 mmol) and stirred for 12.5 hours before concentrating to dryness and subjecting the residue to FCC to give the title compound. (676 mg, 54%). MS (ESI): mass calcd. for C11H16BrNO3S 321.00, m/z found 344.0 [M+Na]+; 1H NMR (600 MHz, CDCl3) δ 8.15 (dd, J=7.9, 1.7, 1H), 7.70 (dd, J=7.8, 1.2, 1H), 7.46-7.39 (m, 1H), 7.39-7.31 (m, 1H), 6.15 (s, 1H), 3.93-3.81 (m, 2H), 1.76 (t, J=6.0, 2H), 1.20 (s, 6H).

Workup

  1. concentrationbefore concentrating to dryness

Sources & evidence

ORD record
ord-85fee97cf58a425da460bda196dd5531
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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