Hydrochloric Acid → HCID 13881294, compound

HRID 2309212Notes

Reaction equation

HRID 2309212 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][CH2:20][CH2:21][OH:22].Cl>C1COCC1>[OH:22][CH2:21][CH2:20][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 313Hydrochloric AcidHCID 90863-Amino-1-propanolHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Product 1

HCID 13881294HCID 13881294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-chlorosulfonyl-6nitrobenzoate (2.80 g, 10 mmol) in 100 ml of THF was cooled to ice temperature and stirred in an ice-bath while a solution of 3-amino-1-propanol (99%) (1.67 g, 22 mmol) was added dropwise over a period of 45 minutes. Stirring in the ice-bath was continued for 30 minutes. The reaction mixture then was acidified by addition of 3.0 ml of 1.2 N HCl. The THF was evaporated under reduced pressure and the residue taken up in 100 ml of ethyl acetate. After extracting this solution with 4×20 ml of saturated NaCl solution, the ethyl acetate was evaporated and the residue recrystallized from a mixture of ethyl acetate and hexane to give 2.70 g (84.9%) of light yellow crystalline product, m.p., 87°-88.5°.

Workup

  1. additionwas added dropwise over a period of 45 minutes
  2. customThe THF was evaporated under reduced pressure
  3. extractionAfter extracting this solution with 4×20 ml of saturated NaCl solution
  4. customthe ethyl acetate was evaporated
  5. customthe residue recrystallized from a mixture of ethyl acetate and hexane
  6. customto give 2.70 g (84.9%) of light yellow crystalline product, m.p., 87°-88.5°

Sources & evidence

ORD record
ord-bee49fd75f5240a28b2096dff1aba828
Source dataset
uspto-grants-1987_09
Patent number
US04694020

Reaction notes

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