Ammonia → 2-[(Aminocarbonyl)amino]-4-methyl-5-(1,4-benzodioxan-6-yl)-3-thiophenecarboxamide

HRID 11423

Reaction equation

HRID 11423 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:11]2[CH:20]=[CH:19][C:14]3[O:15][CH2:16][CH2:17][O:18][C:13]=3[CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].ClC(Cl)(Cl)[C:23]([N:25]=C=O)=[O:24].N>O1CCCC1.CO>[NH2:25][C:23]([NH:1][C:2]1[S:3][C:4]([C:11]2[CH:20]=[CH:19][C:14]3[O:15][CH2:16][CH2:17][O:18][C:13]=3[CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8])=[O:24]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 76400Trichloroacetyl isocyanateHCID 219758672-Amino-4-methyl-5-(1,4-benzodioxan-6-yl)-3-thiophencarboxamide

Product 1

HCID 98807272-[(Aminocarbonyl)amino]-4-methyl-5-(1,4-benzodioxan-6-yl)-3-thiophenecarboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-methyl-5-(1,4-benzodioxan-6-yl)-3-thiophencarboxamide (0.44 g) was dissolved in tetrahydrofuran (10 ml), cooled to 0° C. and trichloroacetylisocyanate (0.11 ml) added dropwise with stirring. Stirring was continued for a further 30 minutes at room temperature and then a solution of ammonia in methanol (8 ml of a 10% solution) was added and stirring was continued for a further 3 h. The solvent was evaporated and the residue treated with ethyl acetate and the product filtered off.

Workup

  1. stirringStirring
  2. stirringstirring
  3. waitwas continued for a further 3 h
  4. customThe solvent was evaporated
  5. additionthe residue treated with ethyl acetate
  6. filtrationthe product filtered off

Sources & evidence

ORD record
ord-0e662e7479ec46efaff48fad19e2d336
Source dataset
uspto-grants-2006_08
Patent number
US07098240B2

Linked notes

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