2-Methoxypropene → 6-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazine

HRID 326596

Reaction equation

HRID 326596 reaction equation
C([Li])CCC.S1CCCSC1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([C:20]#[N:21])[CH:14]=1.[CH3:22][O:23][C:24]([CH3:26])=[CH2:25].[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[O:36][C:35]([CH3:38])([CH3:37])[N:34]=[C:33]([CH:39]3[S:44][CH2:43][CH2:42][CH2:41][S:40]3)[C:32]=2[CH:45]=1>CCCCCC.O1CCCC1>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:25][CH:24]([O:23][CH3:22])[CH3:26])=[C:15]([CH:14]=1)[C:20]#[N:21].[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[O:36][C:35]([CH3:37])([CH3:38])[N:34]=[C:33]([CH:39]3[S:40][CH2:41][CH2:42][CH2:43][S:44]3)[C:32]=2[CH:45]=1

Participants

9

Reactant 5

HCID 83002-MethoxypropeneHCID 104511,3-DithianeHCID 27570145-Bromo-2-hydroxybenzonitrileHCID 197350976-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazineHCID 178418339Butyllithium

Product 2

HCID 197350976-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazineHCID 197351265-Bromo-2-(2-methoxy-2-methylethoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution (13.8 ml) of 1.6M n-butyllithium in hexane was added dropwise to a solution of 1,3-dithian (1.5 g) in anhydrous tetrahydrofuran (35 ml) at -78° C. under an argon atmosphere over 10 minutes. After stirring for 30 minutes, a solution of 5-bromo-2-(2-methoxy-2-methylethoxy)benzonitrile, which was prepared from 4-bromo-2-cyanophenol (m.p. 148°-150° C., 2.48 g) and 2-methoxypropene (1.1 g) according to the same manner as described in Example 29, in anhydrous tetrahydrofuran (5 ml) was added to the mixture. The mixture was treated in the same manner as that in Example 29 to obtain 6-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazine (0.90 g) (Compound 105).

Workup

  1. additionwas added to the mixture
  2. additionThe mixture was treated in the same manner as that in Example 29

Sources & evidence

ORD record
ord-30d90ac680874be6916d41865b13c04c
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Linked notes

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