1,1,1-Trimethoxybutane → HCID 54375564, compound

HRID 845458Notes

Reaction equation

HRID 845458 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[S:11][N:10]=2)=[CH:5][CH:4]=1.[C:18](OC)(OC)([O:22][CH3:23])[CH2:19][CH2:20][CH3:21]>>[CH3:23][O:22][C:18](=[N:17][S:14]([C:12]1[S:11][N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:13]=1)(=[O:16])=[O:15])[CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 14183094HCID 14183094, compound

Product 1

HCID 54375564HCID 54375564, compoundYield 93.6%

Procedure

A mixture of 1.5 g of 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-sulfonamide and 4.1 g of trimethyl orthobutyrate was warmed at reflux for 0.5 hour. The mixture was cooled and triturated with hexane (3x) to give 1.84 g of solid. Recrystallization from cyclohexane/benzene (6:1) gave 1.63 g of fluffy solid. This was combined with 0.7 g sample from another identical small scale reaction. This combined material (2.33 g) had m.p. 159°-161°.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 0.5 hour
  3. temperatureThe mixture was cooled
  4. customtriturated with hexane (3x)

Sources & evidence

ORD record
ord-e8f9361448c7427d979d192170390ee2
Source dataset
uspto-grants-1988_07
Patent number
US04758578

Reaction notes

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