Chloroform → 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

HRID 1159949Notes

Reaction equation

FC(F)(F)[C:3]1[CH:8]=[CH:7]C=CN=1.[C:11]1([CH3:24])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19]([O:22][NH2:23])(=[O:21])=[O:20].FC(F)(F)[C:27]([OH:29])=[O:28].[CH:32](Cl)(Cl)Cl>>[C:8]([O:29][C:27]([NH:23][O:22][S:19]([C:12]1[C:13]([CH3:18])=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=1[CH3:24])(=[O:21])=[O:20])=[O:28])([CH3:7])([CH3:3])[CH3:32]

Participants

Reactant 4

HCID 6212Chloroform

HCID 6422Trifluoroacetic acid

HCID 136199Trifluoromethylpyridine

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

Procedure

2-Trifluoromethylpyridine (7 g, 47.6 mmol) in CHCl3 (100 mL) was treated with O-(mesitylenesulfonyl)-N-hydroxylamine (10.2 g, 47.6 mmol) (obtained from treatment of N-tert-butoxycarbonyl-O-(mesitylsulfonyl)hydroxylamine (15 g, 47.6 mmol) with trifluoroacetic acid (35 mL) and stirred at rt under nitrogen. After 16 h a second batch of O-(mesitylenesulfonyl)-N-hydroxylamine (4.8 g, 22.2 mmol) was added and stirring continued for 4 days. Reaction solution was evaporated to dryness, triturated with ether and filtered. Filtrate was washed with ether and dried to yield 1-amino-2-trifluoromethylpyridinium mesitylenesulfonate (9.6 g, 26.5 mmol).

Sources & evidence

ORD record: ord-2a7e969b3fb64ca789195d18058058c4
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812022B2

Reaction notes

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