Dimethylformamide → HCID 23372733, compound

HRID 1899102Notes

Reaction equation

HRID 1899102 reaction equation
[H-].[Na+].[CH:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:13]=2[C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[CH:8][CH:7]=1)=O.CI.CN(C)[CH:36]=[O:37]>>[CH:36]([CH2:3][NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:13]=2[C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:26][CH:27]=2)=[CH:10][CH:11]=1)=[O:37]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23372713HCID 23372713, compound

Product 1

HCID 23372733HCID 23372733, compound

Procedure

Sodium hydride (60%; 40 mg) was added to an ice-cooled solution of ethyl 5-[4-(formylamino)phenyl]-4-[4-(methylsulfonyl)phenyl]thiophene-2-carboxylate (0.35 g) in N,N-dimethylformamide (10 ml). The mixture was stirred at ambient temperature for 30 minutes, and to the resulting mixture was added methyl iodide (0.23 g) at 5° C. The mixture was stirred at ambient temperature for 1.5 hours and poured into ice-water. The precipitates were collected, washed with water, and dried in vacuo to give ethyl 5-[4-(N-formylmethylamino)phenyl]-4-[4-(methylsulfonyl)phenyl]thiophene-2-carboxylate (0.34 g).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 1.5 hours
  2. customThe precipitates were collected
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-317f4d38c7fd4f9692f7b44db392f9fd
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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