1-Amino-2-propanol → HCID 13881295, compound

HRID 231580Notes

Reaction equation

HRID 231580 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[NH2:18][CH2:19][CH:20]([OH:22])[CH3:21].Cl>C1COCC1>[OH:22][CH:20]([CH3:21])[CH2:19][NH:18][S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 41-Amino-2-propanolHCID 313Hydrochloric AcidHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Product 1

HCID 13881295HCID 13881295, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-chlorosulfonyl-6-nitrobenzoate (2.80g, 10 mmol) in 100 ml of THF was cooled in an ice-bath and stirred while a solution of 1-amino-2-propanol (1.65g, 22 mmol) in 10 ml of THF was added dropwise over a period of 50 minutes. After stirring an additional 30 minutes in the ice-bath, the reaction mixture was acidified by the addition of 3 ml of 1.2N HCl. The THF was evaporated under reduced pressure and the residue taken up in 100 ml of ethyl acetate. After extracting with 4×20 ml of saturated NaCl solution, the ethyl acetate solution was dried over Na2SO4 and the solvent evaporated. The residue was crystallized from a mixture of ethyl acetate and hexane to give 2.02g (63.5%) of yellow crystalline product, m.p., 93.5-95°.

Workup

  1. additionwas added dropwise over a period of 50 minutes
  2. customThe THF was evaporated under reduced pressure
  3. extractionAfter extracting with 4×20 ml of saturated NaCl solution
  4. dry with materialthe ethyl acetate solution was dried over Na2SO4
  5. customthe solvent evaporated
  6. customThe residue was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3eb88ee2dd034ef5a20228993ed08d0b
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

Loading…