ethyl N-(5-ethyl-7-chloro-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate → HCID 20548450, compound

HRID 2058855Notes

Reaction equation

HRID 2058855 reaction equation
[CH2:1]([CH:3]1[CH2:17][C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:16])OCC)[S:10][C:6]=2[CH:5]([Cl:18])[CH2:4]1)[CH3:2].[CH2:19]([NH:22][CH2:23][CH:24]=[O:25])[CH:20]=[CH2:21]>>[CH2:19]([N:22]([CH2:23][CH:24]=[O:25])[C:12]([NH:11][C:9]1[S:10][C:6]2[CH:5]([Cl:18])[CH2:4][CH:3]([CH2:1][CH3:2])[CH2:17][C:7]=2[N:8]=1)=[O:16])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 20548458ethyl N-(5-ethyl-7-chloro-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamateHCID 205484762-Allylaminoacetaldehyde

Product 1

HCID 20548450HCID 20548450, compound

Conditions

Temperature
125 °C

Procedure

Ethyl N-(5-ethyl-7-chloro-4,5,6,7-tetrahydrobenzothiazol-2-yl)-carbamate (0.08 mol) and the dimethyl acetal of 2-allylaminoacetaldehyde (30 ml.) are 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 at 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-allyl-3-(5-ethyl-7-chloro-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-b033b8fce7bd4ecbac30263b927397d4
Source dataset
uspto-grants-1982_03
Patent number
US04319914

Reaction notes

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