Dimethylformamide dimethyl acetal → N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine

HRID 2414128Notes

Reaction equation

HRID 2414128 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>C(#N)C>[CH3:13][N:14]([CH3:16])[CH:15]=[N:10][S:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 12413045-Bromo-2-thiophenesulfonamide

Product 1

HCID 54319951N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred mixture of 5-bromothiophene-2-sulfonamide (24.2 g, 0.10 mol) in acetonitrile (100 ml) was added dimethylformamide dimethyl acetal (14 ml) in acetonitrile (125 ml) dropwise over 0.5 hour. After an additional 0.5 hour the solvent was removed in vacuo. The residue was treated with water and the solid that precipitated was collected and dried, 28.7 g., m.p. 103°-105° C. Recrystallization from 1-chlorobutane gave material with m.p. 104°-106° C.

Workup

  1. customAfter an additional 0.5 hour the solvent was removed in vacuo
  2. additionThe residue was treated with water
  3. customthe solid that precipitated
  4. customwas collected
  5. customdried
  6. customRecrystallization from 1-chlorobutane
  7. customgave material with m.p. 104°-106° C.

Sources & evidence

ORD record
ord-b5ae77c898774c65b6c661607a2c8528
Source dataset
uspto-grants-1988_01
Patent number
US04721794

Reaction notes

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