Sodium hydride → HCID 66957191, compound

HRID 2066674Notes

Reaction equation

Br[C:2]1[N:3]([CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=2)[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>>[I:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:11]2[CH2:12][O:13][C:2]3=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]3[CH2:10]2)=[CH:17][CH:18]=1

Participants

Reactant 2

HCID 24758Sodium hydride

HCID 66956619HCID 66956619, compound

Product 1

HCID 66957191HCID 66957191, compoundYield 78%

Procedure

Ring closure of alcohol 175 with NaH as in Example 2GGG for 5 h, followed by chromatography of the product on silica gel, eluting with 0-1% EtOAc/CH2Cl2 (foreruns) and then with 1.5-2% EtOAc/CH2Cl2, gave 6-[(4-iodophenoxy)methyl]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (176) (78%) as a pale yellow solid: mp (CH2Cl2/pentane triturate) 239-240° C.; 1H NMR [(CD3)2SO] δ 8.09 (s, 1H), 7.60 (dt, J=9.0, 2.7 Hz, 2H), 6.82 (dt, J=9.0, 2.7 Hz, 2H), 4.59 (dd, J=10.9, 2.9 Hz, 1H), 4.44 (dd, J=11.0, 7.2 Hz, 1H), 4.28 (dd, J=12.5, 5.4 Hz, 1H), 4.09 (dd. J=10.0, 6.7 Hz, 1H), 4.06 (dd, J=10.0, 6.7 Hz, 1H), 4.03 (dd, J=12.5, 7.0 Hz, 1H), 2.82 (m, 1H). Anal. (C13H12IN3O4) C, H, N.

Workup

customfor 5 h
washeluting with 0-1% EtOAc/CH2Cl2 (foreruns)

Sources & evidence

ORD record: ord-8e60b59786b341f788d82deb3a1e01a6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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