Ethanol → HCID 21498922, compound

HRID 1730074Notes

Reaction equation

HRID 1730074 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=O)[CH2:7][CH:8]2[C:13](=O)[CH2:12][CH2:11][S:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:18]([NH:20][CH2:21][CH2:22][NH2:23])[CH3:19].C(O)C>Cl.O>[CH2:18]([NH:20][CH2:21][CH2:22][N:23]1[C:6]([C:5]2[CH:16]=[CH:17][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:7][C:8]2[CH2:9][S:10][CH2:11][CH2:12][C:13]1=2)[CH3:19]

Participants

6

Reactant 3

HCID 702EthanolHCID 66071N-EthylethylenediamineHCID 21498918HCID 21498918, compound

Product 1

HCID 21498922HCID 21498922, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 4.0 g (0.012 mole) of 3-(4-bromophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one [Example 2 (a)], 1.3 g of ethylaminoethylamine, 14 ml. of ethanol, and one drop of concentrated hydrochloric acid is heated under reflux for 2.5 hours, cooled to -5°C, and diluted with water. The oil which separates is collected and triturated with water to provide a solid. The resultant solid is recrystallized from ethanol to give off-white crystals of 1-(2-ethylaminoethyl)-2-(4-bromophenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole, m.p. 84° to 85°C.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customThe oil which separates is collected
  3. customtriturated with water
  4. customto provide a solid
  5. customThe resultant solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-f2bc494af6b342b1a03fc93116a6082a
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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