Sulfamide → HCID 12708050, compound

HRID 364223Notes

Reaction equation

HRID 364223 reaction equation
[C:1]([NH:5][S:6]([NH:9][C:10]([CH2:13][C:14]([CH3:17])([CH3:16])C)([CH3:12])[CH3:11])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(N)(N)(=O)=O.ClO[C:25](C)([CH3:27])[CH3:26].[H-].C(N=NC(CC(C)(C)C)(C)C)(C)(C)C>>[C:1]([NH:5][S:6]([NH:9][C:10]12[CH2:11][CH:26]3[CH2:25][CH:27]([CH2:16][CH:14]([CH2:17]3)[CH2:13]1)[CH2:12]2)(=[O:7])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 82267SulfamideHCID 166653HydrideHCID 521297Tert-Butyl hypochloriteHCID 12708049HCID 12708049, compoundHCID 2112238957905-89-2

Product 1

HCID 12708050HCID 12708050, compoundYield 45%

Procedure

Treatment of tertiary alcohols with chlorosulfonyl isocyanate gives monoalkyl sulfamyl chlorides (J. B. Hendrickson and J. Joffe, J. Am Chem. Soc., 95, 4084, 1973). Timberlake used this method to synthesize N-tert-butyl-N'-tert-octylsulfamide in 44% yield (J. W. Timberlake, M. L. Hodges and A. W. Garner, Tetrahedron Lett., 3843, 1973 and J. W. Timberlake, J. Alender, A. W. Garner, M. L. Hodges, C. Ozmeral and S. Szilagyi, J. Org. Chem., 46, 20282, 1981). The sulfamide was oxidized with tert-butyl hypochlorite and sodim hydride to tert-butyl tert-octyldiazene. N-tert-Butyl-N'-(adamant-l-yl) sulfamide was prepared in 45% yield by the same route. There is no evidence it was oxidized to the azo. Apparently, tert-butyl tert-2,2,4,6,6-pentamethyl-4-heptyldiazene was also prepared by this route (J. W. Timberlake and A. W. Garner, J. Org. Chem., 41, 1666, 1976).

Sources & evidence

ORD record
ord-189cb21c80194a6e9824bff97718266d
Source dataset
uspto-grants-1986_08
Patent number
US04604455

Reaction notes

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