Toluene → HCID 14994970, compound

HRID 1654796Notes

Reaction equation

HRID 1654796 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[S:22][C:12]2[CH2:13][N:14]([C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH2:15][CH2:16][C:11]=2[C:10]=1[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30].C(=O)([O-])O.[Na+].[Br:37][CH:38]([CH3:42])[C:39](Br)=[O:40]>C(OCC)(=O)C.O>[Br:37][CH:38]([CH3:42])[C:39]([NH:8][C:9]1[S:22][C:12]2[CH2:13][N:14]([C:17]([CH:19]3[CH2:20][CH2:21]3)=[O:18])[CH2:15][CH2:16][C:11]=2[C:10]=1[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])=[O:40]

Participants

7

Reactant 4

HCID 1140TolueneHCID 79047Propanoyl bromide, 2-bromo-2×HCID 516892Sodium Bicarbonate2×HCID 14994969HCID 14994969, compound

Product 1

HCID 14994970HCID 14994970, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

450 ml of toluene and 150 ml of water were added to 21.83 g of 2-amino-3-(2-chlorobenzoyl)-6-cyclopropanecarbonyl-4,5,6,7-tetrahydro-thieno [2,3-C]pyridine. 10.16 g of sodium hydrogencarbonate was further added, to which 9.5 ml of 2-bromopropionyl bromide was added while heating to 50° to 60° C. Moreover, a sodium hydrogencarbonate aqueous solution (10.6 g of sodium hydrogencarbonate and 150 ml of water) and 5 ml of 2-bromopropionyl bromide were added to complete the reaction. After the completion of the reaction, ethyl acetate was added and the reaction solution was washed once with a saturated saline solution and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 29.9 g of the intended compound (at a quantitative yield).

Workup

  1. additionwas added
  2. temperaturewhile heating to 50° to 60° C
  3. customthe reaction
  4. additionwas added
  5. washthe reaction solution was washed once with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fc00fe03eee04fdf990723682d23bf66
Source dataset
uspto-grants-1995_04
Patent number
US05409909

Reaction notes

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