Piperonyl alcohol → HCID 10309825, compound

HRID 583765Notes

Reaction equation

HRID 583765 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[S:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][C:15]=1[NH:22][C:23](=[O:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:32](O)[C:33]1[CH:41]=[CH:40][C:39]2[O:38][CH2:37][O:36][C:35]=2[CH:34]=1>>[O:38]1[C:39]2[CH:40]=[CH:41][C:33]([CH2:32][O:20][C:19]([C:17]3[S:18][C:14]([CH3:13])=[C:15]([NH:22][C:23](=[O:31])[CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:16]=3)=[O:21])=[CH:34][C:35]=2[O:36][CH2:37]1

Participants

4

Reactant 3

HCID 10322Piperonyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 69693616HCID 69693616, compound

Product 1

HCID 10309825HCID 10309825, compoundYield 73.3%

Procedure

The title compound was prepared according to the procedure described for Example 2 using carbonyldiimidazole (0.26 g, 1.7 mmol), 5-methyl-4-phenylacetylamino-thiophene-2-carboxylic acid from Example 10, Step 1 (0.3 g, 1.1 mmol), and piperonyl alcohol (0.17 g, 1.1 mmol). Acidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration afforded 0.33 g of 5-methyl-4-phenylacetylamino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester. A sample of the product was stirred in 2 M aqueous KHCO3 for several hours, filtered off, rinsed with water, and dried to give product with a mp 191-195° C.

Workup

  1. customThe title compound was prepared
  2. filtrationAcidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration

Sources & evidence

ORD record
ord-c218777c413045d3b8720079f056d9c4
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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