Propanoyl bromide, 2-bromo- → HCID 14986621, compound

HRID 129491Notes

Reaction equation

HRID 129491 reaction equation
[NH2:1][C:2]1[S:13][C:5]2[CH2:6][N:7]([C:10](=[O:12])[CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21].C(=O)([O-])O.[Na+].[Br:28][CH:29]([CH3:33])[C:30](Br)=[O:31]>C1(C)C=CC=CC=1.O>[C:10]([N:7]1[CH2:8][CH2:9][C:4]2[C:3]([C:14](=[O:22])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])=[C:2]([NH:1][C:30](=[O:31])[CH:29]([Br:28])[CH3:33])[S:13][C:5]=2[CH2:6]1)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 79047Propanoyl bromide, 2-bromo-2×HCID 516892Sodium Bicarbonate3×HCID 14986620HCID 14986620, compound

Product 1

HCID 14986621HCID 14986621, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

13.3 g of toluene and 3.66 liters of water were added to 600 g of 2-amino-3-(2-chlorobenzoyl)-6-acetyl-4,5,6,7-tetrahydro-thieno[2,3-C]pyridine, to which 301 g of sodium hydrogencarbonate was further added. While heating to 60° C., 301 ml of 2-bromopropionyl bromide was dropped into the solution. Further, 170 g of sodium hydrogencarbonate and 170 ml of 2-bromopropionyl bromide were added in order to complete the reaction. After cooling down to room temperature, 500 g of sodium hydrogencarbonate was added, after which the organic phase was separated. The aqueous phase was extracted twice with ethyl acetate, followed by combination with the organic phase, washing with water and drying with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resultant solid matter was washed with ether to obtain 800 g of the intended product. 1H-NMR(90 MHz, CDCl3) δ: 1.7-2.4(m,2H), 1.99(d, J=7.2 Hz, 3H), 2.06 and 2.12(each S, total 3H), 3.25-3.7(m,2H), 4.41(q, J=7.2 Hz, 1H), 4,4-4.8(m,2H), 7.0-7.5(m,4H)

Workup

  1. additionwas further added
  2. customthe reaction
  3. temperatureAfter cooling down to room temperature
  4. customafter which the organic phase was separated
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. washwashing with water
  7. dry with materialdrying with anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. washthe resultant solid matter was washed with ether

Sources & evidence

ORD record
ord-8de858dc1f7a46c9866e2850873f006a
Source dataset
uspto-grants-1995_11
Patent number
US05468740

Reaction notes

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