Triethylamine → HCID 20348927, compound

HRID 1282734Notes

Reaction equation

HRID 1282734 reaction equation
Cl.[CH3:2][O:3][NH2:4].C(N(CC)CC)C.[S:12]1[CH:16]=[CH:15][C:14]2[CH:17]([N:21]=[C:22]=[O:23])[CH2:18][CH2:19][CH2:20][C:13]1=2>C(Cl)Cl>[CH3:2][O:3][NH:4][C:22]([NH:21][CH:17]1[C:14]2[CH:15]=[CH:16][S:12][C:13]=2[CH2:20][CH2:19][CH2:18]1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 205373014-Isocyanato-4,5,6,7-tetrahydro-1-benzothiophene

Product 1

HCID 20348927HCID 20348927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

A mixture of 5 grams of methoxyamine hydrochloride in 60 ml. of methylene chloride is stirred and cooled to 15°C., and 6 grams of triethylamine in 15 ml. of methylene chloride is added. After 20 minutes of stirring, 5.38 grams of 4,5,6,7-tetrahydrobenzo[b]thien-4-yl isocyanate is added dropwise. After stirring an additional 0.5 hour at 15°C. to 20°C., the mixture is stirred at room temperature for 0.5 hour. The mix is then filtered, and the filtrate is washed with water and saturated sodium bicarbonate solution. The filtrate is dried (magnesium sulfate) and evaporated to dryness to afford the title compound which is recrystallized from acetone/hexane to give the product with melting point 138.5°C. to 141°C.

Workup

  1. stirringAfter stirring an additional 0.5 hour at 15°C. to 20°C.
  2. stirringthe mixture is stirred at room temperature for 0.5 hour
  3. filtrationThe mix is then filtered
  4. washthe filtrate is washed with water and saturated sodium bicarbonate solution
  5. dry with materialThe filtrate is dried (magnesium sulfate)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-95056ef5e2d34fefa9e3e721d38d2708
Source dataset
uspto-grants-1976_08
Patent number
US03972895

Reaction notes

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