Ethanolamine → HCID 70155322, compound

HRID 2302225Notes

Reaction equation

HRID 2302225 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:15][CH:14]3[CH:12]([O:13]3)[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:17]([CH2:19][NH2:20])[OH:18]>C(O)(C)C>[OH:13][C@H:14]1[C@H:12]([NH:20][CH2:19][CH2:17][OH:18])[CH2:11][N:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:16])=[CH:6][CH:5]=2)(=[O:8])=[O:9])[CH2:15]1

Participants

4

Reactant 2

HCID 700Ethanolamine2×HCID 184598483-(4-Methylbenzene-1-sulfonyl)-6-oxa-3-azabicyclo[3.1.0]hexane

Product 1

HCID 70155322HCID 70155322, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

643.7 g (2.65 mol) of 3-(toluene-4-sulphonyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane are refluxed for 16 hours with 318.5 ml of ethanolamine in 4 l of isopropanol. After TLC checking, a further 35.1 ml (altogether 5.86 mol) of ethanolamine are added to the mixture and it is boiled again until the next morning. The mixture is filtered off with suction whilst hot and the filtrate is concentrated to 3.5 ltr in a rotary evaporator. After seeding and stirring at room temperature, 3.5 l of diisopropyl ether are added and the mixture is stirred at 0° C. for 6 hours. The precipitated crystallizate is filtered off with suction, washed with 250 ml of a mixture of isopropanol/diisopropyl ether (1:1) and twice with 300 ml each of diisopropyl ether and dried overnight in a high vacuum.

Workup

  1. filtrationThe mixture is filtered off with suction whilst hot and the filtrate
  2. concentrationis concentrated to 3.5 ltr in a rotary evaporator
  3. addition3.5 l of diisopropyl ether are added
  4. stirringthe mixture is stirred at 0° C. for 6 hours
  5. filtrationThe precipitated crystallizate is filtered off with suction
  6. washwashed with 250 ml of a mixture of isopropanol/diisopropyl ether (1:1) and twice with 300 ml each of diisopropyl ether
  7. customdried overnight in a high vacuum

Sources & evidence

ORD record
ord-90c5c037090a4c8bb6fddd07e6c5f504
Source dataset
uspto-grants-2002_08
Patent number
US06432948B1

Reaction notes

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