Tert-Butylamine → HCID 58124796, compound

HRID 1971667Notes

Reaction equation

HRID 1971667 reaction equation
CS(O[CH2:6][CH2:7][S:8][CH2:9][C:10]#[C:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)(=O)=O.[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18]>>[CH3:18][C:17]([NH:21][CH2:6][CH2:7][S:8][CH2:9][C:10]#[C:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 58124933HCID 58124933, compound

Product 1

HCID 58124796HCID 58124796, compound

Procedure

A solution of 400 mg of 9d in 8 ml of tert-butyl amine was stirred for 3 days at RT; conversion was completed after that time. The reaction mixture was concentrated and the residue was treated with 30 ml of water and 30 ml of sat. NaHCO3 and the product was extracted into ethyl acetate. The combined organic layers were washed with water, dried and concentrated to provide 354 mg of 9e as essentially pure material, which was used without further purification in the next step. NMR (CDCl3) δ 1.12 (s, 9, tertC4H9), 2.88 (m, 4, 2×CH2), 3.52 (s, 2, CH2), 6.96, 7.18 and 7.22 (3×m, 3, thiophene-H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was treated with 30 ml of water and 30 ml of sat. NaHCO3
  3. extractionthe product was extracted into ethyl acetate
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b605b908819d42f49a0ce23a87bc19b3
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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