Hydrochloric Acid → HCID 13881294, compound

HRID 1906910Notes

Reaction equation

HRID 1906910 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-6-nitrobenzoate (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 1.2N 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-2a08398f81b944a59ce5f803683e22de
Source dataset
uspto-grants-1987_03
Patent number
US04654369

Reaction notes

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