Potassium Carbonate → HCID 66905520, compound

HRID 1691985Notes

Reaction equation

HRID 1691985 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:12]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:12]3[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 771762,6-DichlorobenzothiazoleHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 66905520HCID 66905520, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 2,6-dichlorobenzo[d]thiazole (CAS #3622-23-9, 0.314 g, 3.00 mmol), (S)-pyrrolidin-3-ol (0.314 g, 3.60 mmol), and potassium carbonate (1.24 g, 9.00 mmol) in water/ethanol (10 mL/8 mL) was heated at 150° C. under microwave irradiation for 5 minutes. The reaction mixture was cooled to room temperature then partitioned between dichloromethane and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a crude solid that was purified by crystallization from ethyl acetate/hexane. Crystals were collected by filtration, then dried under vacuum to provide (S)-1-(6-chlorobenzo[d]thiazol-2-yl)pyrrolidin-3-ol. 1H NMR (300 MHz, CD3OD) δ ppm 2.04-2.14 (m, 1H), 2.16-2.29 (m, 1H), 3.48-3.55 (m, 1H), 3.59-3.75 (m, 3H), 4.54-4.59 (m, 1H), 7.26 (dd, J=2, 8 Hz, 1H), 7.40 (d, J=8 Hz, 1H), 7.67 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 255 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen partitioned between dichloromethane and saturated aqueous sodium carbonate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a crude solid that
  7. customwas purified by crystallization from ethyl acetate/hexane
  8. filtrationCrystals were collected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-f535514eac2c4cdc8f0c5dc7b3a47485
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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