HCID 20548455, compound → HCID 20548452, compound

HRID 2058857Notes

Reaction equation

HRID 2058857 reaction equation
[CH2:1]([CH:4]1[CH2:18][C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:17])OCC)[S:11][C:7]=2[CH:6]([C:19]#[N:20])[CH2:5]1)[CH2:2][CH3:3].[CH2:21]([NH:25][CH2:26][CH:27]=[O:28])[CH2:22][CH:23]=[CH2:24]>>[CH2:21]([N:25]([CH2:26][CH:27]=[O:28])[C:13]([NH:12][C:10]1[S:11][C:7]2[CH:6]([C:19]#[N:20])[CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:18][C:8]=2[N:9]=1)=[O:17])[CH2:22][CH:23]=[CH2:24]

Participants

3

Reactant 2

HCID 20548455HCID 20548455, compoundHCID 20548461HCID 20548461, compound

Product 1

HCID 20548452HCID 20548452, compound

Conditions

Temperature
125 °C

Procedure

Ethyl N-(5-propyl-7-cyano-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate (0.08 mol) and the dimethyl acetal of 2-but-3-enylaminoacetaldehyde (30 ml.) as charged into a glass reaction vessel equipped with a stirrer, reflux condenser and gas addition tube. The reaction mixture is blanketed with nitrogen gas and is heated 125° C. for a period of about 8 hours. After this time the reaction mixture is distilled to remove excess starting material. The residue is purified by elution chromatography using ethyl acetate as the eluant. The chromatographed solution is then stripped of solvent to yield the desired product dimethyl acetal of 2-[1-but-3-enyl-3-(5-propyl-7-cyano-4,5,6,7-tetrahydrobenzothiazol-2-yl)ureido]acetaldehyde.

Workup

  1. customequipped with a stirrer
  2. temperaturereflux
  3. additioncondenser and gas addition tube
  4. distillationAfter this time the reaction mixture is distilled
  5. customto remove excess
  6. customThe residue is purified by elution chromatography

Sources & evidence

ORD record
ord-784b6144d9da49ad90744106db569705
Source dataset
uspto-grants-1982_03
Patent number
US04319914

Reaction notes

Loading…