Thionyl Chloride → HCID 70218608, compound

HRID 728366Notes

Reaction equation

HRID 728366 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([OH:10])=O.S(Cl)(Cl)=O.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]([NH2:27])=[O:26])[C:20](=[O:28])[CH2:19]2>CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]([NH2:27])=[O:26])[C:20](=[O:28])[CH:19]2[C:8](=[O:10])[C:4]1[S:5][CH:6]=[CH:7][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 14834753-Methoxythiophene-2-carboxylic acidHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide

Product 1

HCID 70218608HCID 70218608, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

A 2.00 g (12.69 mmoles) sample of 3-methoxy-2-thiophenecarboxylic acid (prepared according to Gronowitz, S., Arkiv. for Kemi. 12:239 (1958)) was reacted with 10 ml of thionyl chloride according to Example 32. Evaporation of excess thionyl chloride left 2.17 g of 3-methoxy-2-thiophenecarbonyl chloride as a crystalline solid, m.p. 86°-88° C. The acid chloride was coupled to 2.16 g (10.24 mmoles) of 5-chloro-2-oxindole-1-carboxamide in the presence of 3.30 g (27 mmoles) 4-(N,N-dimethylamino)pyridine according to the procedure in Example 32. Aqueous acid quench followed by filtration gave a yellow solid which was purified by recrystallization to give 1.04 g (2.96 mmoles, 29% yield) of 5-chloro-3-(3-methoxy-2-thenoyl)-2-oxindole-1-carboxamide as a yellow solid, m.p. 272°-274° C. (acetic acid).

Workup

  1. customEvaporation of excess thionyl chloride
  2. waitleft 2.17 g of 3-methoxy-2-thiophenecarbonyl chloride as a crystalline solid, m.p. 86°-88° C
  3. customAqueous acid quench
  4. filtrationfollowed by filtration
  5. customgave a yellow solid which
  6. customwas purified by recrystallization

Sources & evidence

ORD record
ord-1fb6978a48604dd2a6f19e482a380862
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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