4-Methylbenzyl chloride → HCID 54503915, compound

HRID 1939364Notes

Reaction equation

HRID 1939364 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.[CH3:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.[K+].[Br-]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:22][C:23]2[CH:30]=[CH:29][C:26]([CH3:27])=[CH:25][CH:24]=2)[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1

Participants

4

Reactant 3

HCID 77224-Methylbenzyl chlorideHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 54503915HCID 54503915, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G alkylating with 4-methylbenzyl chloride, in 50% overall yield. This material was crystallized from ether to afford a white solid, mp 92°-94° C.; IR (KBr) 3496, 1659, 1503, 1405, 1304, 1283, 1248, 1063, 801 cm-1 ; 1H NMR (CDCl3) δ2.18-2.36 (m, 5H), 3.91 (q, J=5.7, 2H), 4.83 (dd, J=7.4, 5.7, 1H), 5.12 (s, 2H), 6.90-7.00 (m, 4H), 7.13 (s, 4H); MH+ at m/z=298; Anal. Calc'd for C18H19NO3 : C, 72.71; H, 6.44; N, 4.71. Found: C, 72.71; H, 6.48; N, 4.65.

Workup

  1. customThis material was crystallized from ether
  2. customto afford a white solid, mp 92°-94° C.

Sources & evidence

ORD record
ord-18303779ef114ab9ab9746e81b5e5566
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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