Phosgene → HCID 22496346, compound

HRID 601143Notes

Reaction equation

HRID 601143 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[OH-].[K+].C(Cl)(Cl)=[O:20]>O>[C:11]1([C:7]2[S:6][C:5]3[C:3](=[O:4])[O:2][C:1](=[O:20])[NH:10][C:9]=3[CH:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 22496346HCID 22496346, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methyl-3-amino-5-phenylthiophene-2-carboxylate (0.25 g, 1.07 mmol) in water (6 mL) was reacted with potassium hydroxide (0.12 g, 2.14 mmol) at 90° C. for 24 hours. The reaction was cooled to 0° C. and phosgene (1.9M in toluene, 0.70 mL, 1.40 mmol) was added dropwise. After stirring at room temperature for 1 hour, the resulting solid was collected by filtration, washed with excess water and dried to give the title compound as a tan solid (0.175 g, 65%).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with excess water
  3. customdried

Sources & evidence

ORD record
ord-35f0f8ff129d473cafb4fe9af321f690
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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