Water → HCID 22048222, compound

HRID 1830839Notes

Reaction equation

HRID 1830839 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][S:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[Cl-:21].[Al+3].[Cl-:23].[Cl-].[C:25]1([CH3:31])C=CC=C[CH:26]=1.O>O1CCCC1>[Cl:21][C:26]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:3]2[C:4]3[CH2:9][CH2:8][S:7][CH2:6][C:5]=3[S:10][C:2]2=[N:1][C:25]=1[CH2:31][Cl:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 6451240Aluminum(III) ChlorideHCID 22048198HCID 22048198, compound

Product 1

HCID 22048222HCID 22048222, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-4,5-dihydro-3-(4-methoxybenzoyl)-7H-thieno[2,3-c]thiopyrane (9.557 kg), 1,3-dicholoroacetone (4.172 kg) in tetrahydrofuran (48.79 L) was added aluminum chloride (5.424 kg) divided in 4 portions. Then, the mixture was stirred under reflux for 4.5 hours and toluene (38.74 L) was added at 10° C. or lower, followed by dropwise addition of water (47.79 L). After addition of toluene (56.83 L), the mixture was stirred and the organic layer was separated, washed with water, saturated aqueous sodium bicarbonate solution and then water. The solvent was distilled off until the content became 34.61 kg. Methanol (57.34 L) was added dropwise thereto at about 25° C. The mixture was stirred at 5° C. for 1 hour and crystals deposited were filtered off to obtain the titled compound (11.055 kg, 88.3%). 1H (CDCl3) δ: 2.18 (2H, t, J=5.7 Hz), 2.68 (2H, t, J=5.7 Hz), 3.90 (5H, s), 4.94 (2H, s), 7.01 (2H, d, J=8.7 Hz), 7.16 (2H, d, J=8.7 Hz).

Workup

  1. temperatureunder reflux for 4.5 hours
  2. stirringthe mixture was stirred
  3. customthe organic layer was separated
  4. washwashed with water, saturated aqueous sodium bicarbonate solution
  5. distillationThe solvent was distilled off until the content
  6. additionMethanol (57.34 L) was added dropwise
  7. customat about 25° C
  8. stirringThe mixture was stirred at 5° C. for 1 hour
  9. filtrationcrystals deposited were filtered off

Sources & evidence

ORD record
ord-6e5cb4870aa245a3a592aea504c48204
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

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