Sodium hydride → HCID 12708050, compound

HRID 1762223Notes

Reaction equation

HRID 1762223 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-].[Na+].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 24758Sodium hydrideHCID 82267SulfamideHCID 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 sodium hydride to tert-butyl tert-octyldiazene. N-tert-Butyl-N'-(adamant-1-y1 ) 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-f8eb4f8c33c34f3795c2a36f1fa51ce6
Source dataset
uspto-grants-1989_05
Patent number
US04831096

Reaction notes

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