Acetonitrile → HCID 178483224, compound

HRID 1681480Notes

Reaction equation

HRID 1681480 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]2[C:19](OCC)=[C:18]([C:23](=[O:27])[N:24]([CH3:26])[CH3:25])[S:17](=[O:29])(=[O:28])[N:16]=2)=[CH:7][CH:6]=1)[CH3:3].C(#[N:32])C>>[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]2[C:19]([NH2:32])=[C:18]([C:23](=[O:27])[N:24]([CH3:26])[CH3:25])[S:17](=[O:29])(=[O:28])[N:16]=2)=[CH:7][CH:6]=1)[CH3:3]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 178467035HCID 178467035, compound

Product 1

HCID 178483224HCID 178483224, compound

Procedure

Into a solution of 3-[2-[(5-dimethylaminomethyl-2-furanyl)methylthio]ethyl]amino-4-ethoxy-5-dimethylcarbamylisothiazole-1,1-dioxide (1.4 g, 3.2 mmol) in acetonitrile (12 ml) warmed at 65° C., ammonia gas was slowly bubbled over a 1-2 hour period. Solvent was evaporated, residue chromatographed on silica gel eluting with 3-5% methanol/chloroform to give 0.96 g of title compound which could be crystallized from nitromethane/ether, mp 101°-104°.

Workup

  1. customammonia gas was slowly bubbled over a 1-2 hour period
  2. customSolvent was evaporated
  3. customresidue chromatographed on silica gel eluting with 3-5% methanol/chloroform

Sources & evidence

ORD record
ord-58e20f6be2da4f7bb57ad09705558051
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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