Ammonia → HCID 63108316, compound

HRID 1188013Notes

Reaction equation

HRID 1188013 reaction equation
C(O[C:4]([C:6]1[S:7][C:8]([Cl:11])=[CH:9][CH:10]=1)=[NH:5])C.[OH:12][CH:13](O)[C:14](=O)[CH3:15].[NH3:18]>CO>[Cl:11][C:8]1[S:7][C:6]([C:4]2[NH:5][C:14]([CH2:13][OH:12])=[CH:15][N:18]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 131809821,1-Dihydroxypropan-2-oneHCID 60985494HCID 60985494, compound

Product 1

HCID 63108316HCID 63108316, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
77 °C

Procedure

A mixture of 5-chlorothiophene-2-carboximidic acid ethyl ester (38.7 g, 0.171 mol), 15.4 g of dihydroxyacetone (0.171 mol) and 102.18 g of gaseous ammonia (6.0 mol) in 500 ml of methanol was heated at 77° C. in a high-pressure reactor. After cooling and evaporation under vacuum, ammonium chloride was filtered and washed with methanol. The filtrate was concentrated under vacuum and yielded 35.1 g of crude product, which was used without further purification.

Workup

  1. temperatureAfter cooling
  2. customevaporation under vacuum, ammonium chloride
  3. filtrationwas filtered
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-38e4694f938a44e5b272361aea78e882
Source dataset
uspto-grants-2014_03
Patent number
US08673955B2

Reaction notes

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