Ethanolamine → HCID 22733781, compound

HRID 2084981Notes

Reaction equation

HRID 2084981 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13]>ClCCl.CCOC(C)=O>[OH:2][CH2:1][CH2:3][NH:4][S:21]([C:18]1[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=1)(=[O:22])=[O:23]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 22733781HCID 22733781, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethanolamine (0.68 g, 11 mmol) and triethylamine (1.10 g, 10.9 mmol) in dichloromethane (20 mL) was added 4-nitrobenzenesulfonyl chloride (2.20 g, 9.9 mmol) portionwise with stirring. The resulting clear yellow solution was stirred at room temperature for 15 min. The clear yellow solution was diluted with equal volume of EtOAc and washed with water and then with 5% HCl. The organic phase was evaporated to dryness to give 1.36 g of light yellow crystalline solid which was dried and used without further purification. δH (200 MHz, DMSO-d6) 2.90 [2H, m, NHCH2CH2OH], 3.36 [2H, m, NHCH2CH2OH], 4.75 [1H, t, OH], 8.00 [1H, m, NH], 8.02 and 8.38 [2×2H, q (A2B2), 2×Nosyl CH].

Workup

  1. stirringThe resulting clear yellow solution was stirred at room temperature for 15 min
  2. washwashed with water
  3. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-0840bf9c01f14ff0ae9fe04c0bb5bbc2
Source dataset
uspto-grants-2004_04
Patent number
US06716961B2

Reaction notes

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