Tetrahydrofuran → 61073-23-2

HRID 1283317Notes

Reaction equation

HRID 1283317 reaction equation
[NH2:1][N:2]1[C:6]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]1=[NH:12].[O:13]1C[CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C(Cl)(=O)CC>O>[NH2:1][N:2]1[C:6]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]1=[N:12][C:14](=[O:13])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 203681332-Imino-4-methyl-1,3-benzothiazol-3(2H)-amine

Product 1

HCID 2036811261073-23-2

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3.6 g. portion of 3-amino-2-imino-4-methylbenzothiazoline was dissolved in about 100 ml. of tetrahydrofuran, and 2.2 g. of triethylamine was added. The reaction mixture was cooled in an ice bath, and 2 g. of propionyl chloride, dissolved in 2 ml. of tetrahydrofuran, was added dropwise while the mixture was stirred. After the addition was complete, the reaction mixture was stirred at ice bath temperature for about 3 hours, and was then diluted with an equal volume of water. The tetrahydrofuran was removed under vacuum, and the remaining aqueous mixture was filtered to recover the product. After recrystallization from ethanol, the yield of purified product was 3.2 g. of 3-amino-4-methyl-2-propionyliminobenzothiazoline, m.p. 175°-76°C. The product was identified by nuclear magnetic resonance and ultraviolet analysis and by elemental microanalysis.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred at ice bath temperature for about 3 hours
  4. customThe tetrahydrofuran was removed under vacuum
  5. filtrationthe remaining aqueous mixture was filtered
  6. customto recover the product
  7. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-ee0622ee021e4c978a80b09ae497d49e
Source dataset
uspto-grants-1976_08
Patent number
US03974286

Reaction notes

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