Tert-Butylamine → HCID 58981124, compound

HRID 1181801Notes

Reaction equation

HRID 1181801 reaction equation
[C:1]([NH:5][S:6]([C:9]1[N:10]=[CH:11][N:12]([CH3:14])[CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1C=C(S(Cl)(=O)=O)N=C1.C(N)(C)(C)C.C1C[O:33][CH2:32]C1>>[C:1]([NH:5][S:6]([C:9]1[N:10]=[C:11]([CH:32]=[O:33])[N:12]([CH3:14])[CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6385Tert-ButylamineHCID 8028TetrahydrofuranHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 59315872HCID 59315872, compound

Product 1

HCID 58981124HCID 58981124, compound

Procedure

Step A) Preparation of N-(tert-butyl)-1-methyl-1H-imidazole-4-sulfonamide: A solution of 5.2 gm (29 mmol) 1-methyl-1H-imidazole-4-sulfonyl chloride in 30 mL THF was cooled in ice water while 7 mL tert-butylamine was added dropwise. The solution was warmed to room temperature and stirred overnight. Solids were filtered and rinsed with additional THF. The filtrate was concentrated to give a white solid that was recrystallized from water and dried in vacuo to give 4.8 gm of the subtitle compound, 1H NMR (d6-DMSO) δ 7.75 (s, 1H), 7.65 (s, 1H), 7.2 (s, 1H), 3.7 (s, 3H), 1.1 (s, 9H).

Workup

  1. additionwas added dropwise
  2. filtrationSolids were filtered
  3. washrinsed with additional THF
  4. concentrationThe filtrate was concentrated
  5. customto give a white solid
  6. customthat was recrystallized from water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-eacc6bf437b3424f8bd78ed2c023c39d
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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