Thionyl Chloride → HCID 70221743, compound

HRID 728368Notes

Reaction equation

HRID 728368 reaction equation
S(Cl)(Cl)=O.[C:5]([O:8][C:9]1[CH:10]=[C:11]([C:14]([OH:16])=O)[S:12][CH:13]=1)(=[O:7])[CH3:6].C(OC1C=C(C(Cl)=O)SC=1)(=O)C.[Cl:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:39]([NH2:41])=[O:40])[C:34](=[O:42])[CH2:33]2>CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:39]([NH2:41])=[O:40])[C:34](=[O:42])[CH:33]2[C:14](=[O:16])[C:11]1[S:12][CH:13]=[C:9]([O:8][C:5](=[O:7])[CH3:6])[CH:10]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 15007375HCID 15007375, compoundHCID 212660205-(Chlorocarbonyl)thiophen-3-yl acetate

Product 1

HCID 70221743HCID 70221743, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

The title compound was prepared according to the procedure of Example 32. The reaction of 15 ml of thionyl chloride with 3.58 g (19.23 mmoles) of 4-acetoxy-2-thiophenecarboxylic acid (prepared according to Bohlmann, F., et al., Chem. Ber. 106:497 (1973)) gave a yellow oil. A 3.32 g (16.22 mmoles) sample of 4-acetoxy-2-thiophenecarbonyl chloride was coupled to 2.85 g (13.52 mmoles) of 5-chloro-2-oxindole-1-carboxamide in the presence of 4.16 g (34.07 mmoles) 4-(N,N-dimethylamino)pyridine to give 5.40 g of crude yellow product. Purification by recrystallization gave 4.18 g (11.02 mmoles, 82%) of pure title compound as a yellow solid, m.p. 222°-224° C. (acetic acid).

Workup

  1. customThe title compound was prepared
  2. customgave a yellow oil
  3. customto give 5.40 g of crude yellow product
  4. customPurification
  5. customby recrystallization

Sources & evidence

ORD record
ord-f90b6494316c40c8b7d604517f348332
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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