Sodium hydride → N,N-Dimethyl-N'-[5-(4-methoxybenzylthio)thiophene-2-sulfonyl]formamidine

HRID 2414129Notes

Reaction equation

HRID 2414129 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:13][N:14]([CH3:26])[CH:15]=[N:16][S:17]([C:20]1[S:21][C:22](Br)=[CH:23][CH:24]=1)(=[O:19])=[O:18]>CN(C=O)C.O>[CH3:13][N:14]([CH3:26])[CH:15]=[N:16][S:17]([C:20]1[S:21][C:22]([S:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:23][CH:24]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 54319951N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine

Product 1

HCID 53734177N,N-Dimethyl-N'-[5-(4-methoxybenzylthio)thiophene-2-sulfonyl]formamidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 4-methoxy-α-toluenethiol (7.7 g, 0.05 mol) in DMF (10 ml) was added dropwise to a stirred mixture of sodium hydride (2.50 g, 50% oil dispersion, 0.054 mol) in DMF (40 ml). When gas evolution was complete, N,N-dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine (14.85 g; 0.05 mol) was added and the resulting mixture was stirred for 1 hour at 25° C. The reaction mixture was diluted with water and the solid that separated was collected, washed with water and dried to give 15.36 g., m.p. 92°-101° C. Recrystallization from 1-chlorobutane gave material with m.p. 110°-111.5° C.

Workup

  1. customthe solid that separated
  2. customwas collected
  3. washwashed with water
  4. customdried
  5. customto give 15.36 g
  6. customRecrystallization from 1-chlorobutane
  7. customgave material with m.p. 110°-111.5° C.

Sources & evidence

ORD record
ord-f8b47f6fca01497789d745aad5a9cfa5
Source dataset
uspto-grants-1988_01
Patent number
US04721794

Reaction notes

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