Diethanolamine → HCID 86601655, compound

HRID 1865810Notes

Reaction equation

Cl[C:2]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH3:9])=[O:5].[NH:27]([CH2:31][CH2:32][OH:33])[CH2:28][CH2:29][OH:30]>>[OH:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][OH:33])[C:2]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH3:9])=[O:5]

Participants

Reactant 2

HCID 8113Diethanolamine

HCID 86601656HCID 86601656, compound

Product 1

HCID 86601655HCID 86601655, compoundYield 95%

Procedure

Reaction of 21 (1.45 g, 3.75 mmol) with diethanolamine (1.67 g) as above gave 2-[bis(2-hydroxyethyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)propyl]benzamide (22) (1.62 g, 95%): as a yellow foam; 1H NMR [(CD3)2SO] δ 8.96 (m, 1 H, CONH), 8.66 (d, J=2.8 Hz, 1 H, H-4), 8.31 (d, J=2.8 Hz, 1 H, H-6), 4.95 (m, 2 H), 4.56 (m, 1 H), 3.79-3.16 (m, 14 H), 1.80-1.45 (m, 8 H); 13C NMR δ 166.2, 148.1, 143.6, 139.3, 133.8, 128.9, 123.8, 98.5, 64.8, 61.7, 58.5, 54.6, 37.3, 30.6,29.2, 25.4, 19.6. HRMS (FAB) Calcd. For C19H29N4O6 [M+H+] m/z 457.1935. Found; 457.1939.

Sources & evidence

ORD record: ord-2e71e483a34443f99a31897b505740e3
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629332B2

Reaction notes

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