2-(Methylamino)acetaldehyde → HCID 20548469, compound

HRID 2058860Notes

Reaction equation

HRID 2058860 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:15])OCC.[CH3:16][NH:17][CH2:18][CH:19]=[O:20]>>[CH3:16][N:17]([CH2:18][CH:19]=[O:20])[C:11]([NH:10][C:2]1[S:1][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=1)=[O:15]

Participants

3

Reactant 2

HCID 133161322-(Methylamino)acetaldehydeHCID 17191182Carbamic acid, (4,5,6,7-tetrahydro-2-benzothiazolyl)-, ethyl ester

Product 1

HCID 20548469HCID 20548469, compound

Conditions

Temperature
120 °C

Procedure

Ethyl N-(4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate (13.6 grams; 0.06 mol) and the dimethyl acetal of 2-methylaminoacetaldehyde (20 mol.) were charged into a glass reaction vessel equipped with a stirrer, reflux condenser and gas addition tube. The reaction mixture was blanketed with nitrogen gas and heated at 120° C. for a period of 24 hours. Since starting material remained, the mixture was heated for an additional 48 hours and then for an additional 18 hours. After this time the reaction mixture was distilled to remove excess starting material. The residue was purified by chromatography using ethyl acetate as the eluant on silica gel adsorbant yielding the desired product, dimethyl acetal of 2-[1-methyl-3-(4,5,6,7-tetrahydrobenzothiazol-2-yl)ureido]acetaldehyde; (8.9; melting point 89°-92° C.). The structure of the product was verified by infrared and NMR spectroscopy.

Workup

  1. customequipped with a stirrer
  2. temperaturereflux
  3. additioncondenser and gas addition tube
  4. temperaturethe mixture was heated for an additional 48 hours
  5. distillationAfter this time the reaction mixture was distilled
  6. customto remove excess
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-3f9176f82aaf4204baebed2457d27e41
Source dataset
uspto-grants-1982_03
Patent number
US04319914

Reaction notes

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