Sodium Hydroxide → HCID 14047794, compound

HRID 1383032Notes

Reaction equation

HRID 1383032 reaction equation
O[CH2:2][N:3]1[C:7](=[O:8])[CH2:6][CH:5]([S:9][C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)[C:4]1=[O:25].CS(Cl)(=O)=O.[C:31]([C:35]1[CH:36]=[C:37]([SH:46])[CH:38]=[C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:40]=1[OH:41])([CH3:34])([CH3:33])[CH3:32].[OH-].[Na+]>C(OC(=O)C)C.CCCCCCC.C(N(CC)CC)C>[C:31]([C:35]1[CH:36]=[C:37]([S:46][CH2:2][N:3]2[C:7](=[O:8])[CH2:6][CH:5]([S:9][C:10]3[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=3)[C:4]2=[O:25])[CH:38]=[C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:40]=1[OH:41])([CH3:34])([CH3:33])[CH3:32]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 21273723HCID 21273723, compound

Product 1

HCID 14047794HCID 14047794, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

The procedure of Example 3 was repeated using 10.0 grams of N-(hydroxymethyl)-2-(3,5-di-tert-butyl-4-hydroxyphenylthio)succinimide, 2.33 ml of methanesulfonylchloride, 5.72 ml of triethylamine, 6.52 grams of 3,5-di-tert-butyl-4-hydroxybenzene thiol and 1.09 grams of sodium hydroxide. Flash column chromatography (SiO2, 5:1 heptane:ethylacetate) afforded 7.09 grams of product as white solid, m.p. 138°-140° C.

Sources & evidence

ORD record
ord-4b79d870dcbb4577bb2ace634e38abfc
Source dataset
uspto-grants-1989_02
Patent number
US04808644

Reaction notes

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