2,2-Dimethoxyethylmethylamine → HCID 13021501, compound

HRID 2287231Notes

Reaction equation

HRID 2287231 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].[Cl:9][C:10]1[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=1[O:12][CH:13]([C:15]1[S:19][C:18]([N:20]=[C:21]=[O:22])=[N:17][N:16]=1)[CH3:14]>C1C=CC=CC=1>[Cl:9][C:10]1[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=1[O:12][CH:13]([C:15]1[S:19][C:18]([NH:20][C:21](=[O:22])[N:5]([CH3:6])[CH2:4][CH:3]([O:7][CH3:8])[O:2][CH3:1])=[N:17][N:16]=1)[CH3:14]

Participants

4

Reactant 2

HCID 85032,2-DimethoxyethylmethylamineHCID 13021505HCID 13021505, compound

Product 1

HCID 13021501HCID 13021501, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methylaminoacetaldehyde dimethylacetal (4.2 grams, 0.035 mole) was slowly added at ambient temperature to a 30 milliliter benzene solution containing 9.9 grams (0.035 mole) of the 5-[1-(2-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer (prepared above). The resulting solution was refluxed for 20 minutes, cooled and topped on a roto-vac at 70° C. to 13.4 grams of an orange oil which partially crystallized upon standing. The entire sample was recrystallized from a minimum amount of ethylacetate/hexane solution. The crystals were filtered off and dried in a vacuum oven at 80° C. to give 10.2 grams of white crystals of 3-[5-(2-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-1(2,2-dimethoxyethyl)urea. (Melting point 101°-104° C.).

Workup

  1. additioncontaining
  2. temperatureThe resulting solution was refluxed for 20 minutes
  3. temperaturecooled
  4. custompartially crystallized
  5. customThe entire sample was recrystallized from a minimum amount of ethylacetate/hexane solution
  6. filtrationThe crystals were filtered off
  7. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-5d082f9730a743acaa1d20770a79b214
Source dataset
uspto-grants-1981_05
Patent number
US04269983

Reaction notes

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