Thiophosgene → HCID 11219088, compound

HRID 457575Notes

Reaction equation

HRID 457575 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([CH:12]=1)[NH2:11])(=[O:5])=[O:4])[CH3:2].[C:15](Cl)(Cl)=[S:16].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([N:11]=[C:15]=[S:16])[CH:12]=1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 792785-Ethylsulphonyl-o-anisidineHCID 516892Sodium Bicarbonate

Product 1

HCID 11219088HCID 11219088, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-(ethylsulfonyl)-2-methoxyaniline (15.6 g, 72.5 mmol) in dichloromethane (100 mL) was added dropwise over 1 h to a stirred solution of thiophosgene (9 g, 78.0 mmol) in dichloromethane (300 mL) at RT. After the addition was complete, the reaction was stirred for 2 h. Subsequently, saturated aqueous sodium bicarbonate (200 mL) was added, and the reaction was stirred for an additional 1 h. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (18.6 g, 72.4 mmol) as a tan solid. 1H NMR (400 MHz, d6-DMSO): δ 7.78 (dd, J1=2.2, J2=8.8, 1H), 7.71 (d, J=2.2, 1H), 7.35 (d, J=8.8, 1H), 3.95 (s, 3H), 3.22 (q, J=7.4, 2H), 1.02 (t, J=7.3, 3H).

Workup

  1. additionAfter the addition
  2. stirringthe reaction was stirred for an additional 1 h
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37438adeb39047419d7ee8aa13b44255
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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