Benzyl Chloride → HCID 53003028, compound

HRID 1939375Notes

Reaction equation

HRID 1939375 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[K+].[Br-]>>[CH2:22]([N:15]1[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]1=[O:17])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 53003028HCID 53003028, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with benzyl chloride, in 49% overall yield and crystallized from ether/hexane to produce a white solid, mp 83°-85.5° C.; IR (KBr) 3213, 1680, 1505, 1399, 1250, 1050, 753 cm-1 ; 1H NMR (CDCl3) δ2.17-2.38 (m, 3H), 3.92 (q, J=5.7 Hz, 2H), 4.84 (dd, J=7.5, 5.6 Hz, 1H), 5.16 (s, 2H), 6.86-7.03 (m, 4H), 7.21-7.37 (m, 5H); MH+ at m/z=284; Anal. Calc'd for C17H17NO3 : C, 72.07; H, 6.05; N, 4.94. Found: C, 72.08; H, 6.20; N, 4.87.

Workup

  1. customoverall yield
  2. customcrystallized from ether/hexane
  3. customto produce a white solid, mp 83°-85.5° C.

Sources & evidence

ORD record
ord-3bc5914e9862412e9fd786c9c926d98b
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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