1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Phenyl-4-(4-phenylthiazol-2-ylamino)butan-2-ol

HRID 2037439Notes

Reaction equation

HRID 2037439 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[NH2:13][CH2:14][CH2:15][C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:18])[CH3:17].C1CCN2C(=NCCC2)CC1>>[C:19]1([C:16]([OH:18])([CH2:15][CH2:14][NH:13][C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)[CH3:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27613592-Chloro-4-phenylthiazoleHCID 249751014-Amino-2-phenylbutan-2-ol

Product 1

HCID 581096672-Phenyl-4-(4-phenylthiazol-2-ylamino)butan-2-olYield 20.5%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-phenylthiazole (300 mg, 1.5 mmol), 4-amino-2-phenyl-butan-2-ol (294 mg, 1.5 mmol) and DBU (1.5 mL) was heated to 100° C. under N2 in a microwave for 2 h. After the material was consumed, the mixture was neutralized with 1 N HCl solution (5 mL), extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried over Na2SO4 and concentrated to leave a residue, which was purified by column chromatography (1:2 petroleum ether/EtOAc) to afford 2-phenyl-4-(4-phenylthiazol-2-ylamino)butan-2-ol (100 mg, 20%).

Workup

  1. customAfter the material was consumed
  2. extractionextracted with CH2Cl2 (3×5 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. customto leave a residue, which
  6. customwas purified by column chromatography (1:2 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-ab91b83594194fdcb12ef5714d802325
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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