Ammonia → Toluene

HRID 1514756Notes

Reaction equation

[CH:1]([Si:4]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[O:5][CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:19]2[CH:20]=[C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:31]O)[CH:22]=[CH:23][C:18]2=[N:17][N:16]=1)([CH3:3])[CH3:2].CS(OS(C)(=O)=O)(=O)=O.C([N:50](CC)CC)C.N.CO>C1(C)C=CC=CC=1.O>[CH:36]([Si:4]([CH:1]([CH3:2])[CH3:3])([CH:33]([CH3:34])[CH3:35])[O:5][CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:19]2[CH:20]=[C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:31][NH2:50])[CH:22]=[CH:23][C:18]2=[N:17][N:16]=1)([CH3:37])[CH3:38].[C:10]1([CH3:15])[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a slurry of benzyl alcohol of Example 8 (25.0 g, 0.044 moles) in toluene (250 ml), was added methanesulfonic anhydride (10.77 g, 0.062 moles) then cooled to 5° C. Triethylamine (6.93 g, 0.068 moles) was added over 30 minutes and stirred at this temperature for 3 hours. The resultant solution was added to 7M ammonia in methanol solution (316 ml, 2.21 moles) and stirred for 16 hours. Water (250 ml) was added and the organic phase washed with water (250 ml). The aqueous phases were extracted with toluene (125 ml) and the combined organics were dried by azeotropic distillation under reduced pressure to leave the title compound as a clear brown solution in toluene (125 ml) (assumed quantitative yield).

Workup

stirringstirred for 16 hours
washthe organic phase washed with water (250 ml)
extractionThe aqueous phases were extracted with toluene (125 ml)
customthe combined organics were dried by azeotropic distillation under reduced pressure

Sources & evidence

ORD record: ord-838f9e200a2d4465b13fafd4f8e4a533
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222273B2

Reaction notes

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