Tert-Butylamine → HCID 13473211, compound

HRID 2164619Notes

Reaction equation

HRID 2164619 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][C:8]2[N:9]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:11][C:7]=2[CH:6]=1.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>C(#N)C.CO>[C:19]([NH:23][CH2:18][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:17]=[CH:16][C:8]2[N:9]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:11][C:7]=2[CH:6]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 13473207HCID 13473207, compound

Product 1

HCID 13473211HCID 13473211, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-(2,3-epoxypropoxy)benzothiazole-2-sulfonamide (1.14 gm, 4.0 mmol) in acetonitrile (16 mL) and methanol (4 mL) containing t-butylamine (0.88 mL, 0.4 mmol) was warmed at 50° C. for 15-20 hours. The solvents were evaporated and the residue (1.1 gm) was chromatographed on silica gel eluting with 20-30% methanol/chloroform (V/V). The appropriate fractions were combined and evaporated. The residue was digested in acetonitrile, cooled and the produce collected (0.62 gm), m.p. 195°-196° C.

Workup

  1. customThe solvents were evaporated
  2. customthe residue (1.1 gm) was chromatographed on silica gel eluting with 20-30% methanol/chloroform (V/V)
  3. customevaporated
  4. temperaturecooled
  5. customthe produce collected (0.62 gm), m.p. 195°-196° C.

Sources & evidence

ORD record
ord-8c421d6f665c478aa4fabcf32d497dd0
Source dataset
uspto-grants-1985_03
Patent number
US04505923

Reaction notes

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