2-Thiophenesulfonyl chloride → HCID 20085618, compound

HRID 1608818Notes

Reaction equation

HRID 1608818 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)=[O:5].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[S:23]([Cl:26])(=[O:25])=[O:24]>>[ClH:26].[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][S:23]([C:19]1[S:18][CH:22]=[CH:21][CH:20]=1)(=[O:25])=[O:24]

Participants

3

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085618HCID 20085618, compoundYield 36.8%

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 6B using 1.50 g (0.00651 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide, prepared as in Example 6A, and 1.62 g (0.00847 mol) of 2-thiophenesulfonyl chloride, with the exception that after removing ethyl acetate, the resultant residue was dissolved in methanol containing hydrochloric acid and diethyl ether. The resulting solution was reduced to dryness under reduced pressure and the product was recrystallized from water and dried for approximately 8 hours at 100° C. under reduced pressure to provide 0.99 g of the desired titled compound (m.p. 210°-213° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customwith the exception that after removing ethyl acetate
  3. dissolutionthe resultant residue was dissolved in methanol
  4. additioncontaining hydrochloric acid and diethyl ether
  5. customthe product was recrystallized from water
  6. customdried for approximately 8 hours at 100° C. under reduced pressure

Sources & evidence

ORD record
ord-588543853e4d46fb953409625151e199
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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