Triethylamine → HCID 178471604, compound

HRID 26128Notes

Reaction equation

HRID 26128 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Cl[C:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[S:21](=[O:29])(=[O:28])[N:20]=1>O1CCOCC1>[O:28]=[S:21]1(=[O:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:19]([NH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64783Pseudosaccharin chlorideHCID 126496614-Aminobutyrate ethyl hydrochloride

Product 1

HCID 178471604HCID 178471604, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.07 ml (29.2 mM) of triethylamine is added to 5.0 g. (29.2 mM) of ethyl 4-aminobutyrate hydrochloride, suspended in 75 ml of dioxane. After stirring for 5 minutes, 5.88 g. (29.2 mM) of 3-chloro-1,2-benzisothiazole 1,1-dioxide is added and the mixture is refluxed for one hour. The solvent is evaporated in vacuo and the residue is taken up in chloroform, washed with water, and evaporated to dryness. The residual 4-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]-butanoic acid, ethyl ester is recrystallized from 40 ml. of methanol/water, yield 3.72 g., m.p. 125°-127°.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. customThe solvent is evaporated in vacuo
  3. washwashed with water
  4. customevaporated to dryness
  5. customThe residual 4-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]-butanoic acid, ethyl ester is recrystallized from 40 ml

Sources & evidence

ORD record
ord-2073cfa5dfc644b1b7a11fd14d15da28
Source dataset
uspto-grants-1979_04
Patent number
US04148798

Reaction notes

Loading…