Triethylamine → HCID 20450026, compound

HRID 358051Notes

Reaction equation

HRID 358051 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[S:12][CH2:13][CH2:14][C:15]([OH:17])=O.C(N(CC)CC)C.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(Cl)Cl>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:11]1[C:5]2[CH:6]=[C:7]([NH:10][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:8]=[CH:9][C:4]=2[NH:3][C:15](=[O:17])[CH2:14][CH2:13][S:12]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 70508087HCID 70508087, compound

Product 1

HCID 20450026HCID 20450026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 138.2 g of 3-[(2,5-diaminophenyl)(2-chlorophenyl)methylthio]propionic acid dihydrochloride in 8.6 l of dry methylene chloride is treated at -5° with 94 ml of triethylamine. Subsequently, there are successively added thereto at 0° to 2° 129.1 ml of ethyl chloroformate and 188 ml of triethylamine. The cooling means is then removed and the mixture is stirred for a further 90 minutes. The mixture is evaporated and the residue is chromatographed on 1.44 kg of silica gel. Elution is carried out with chloroform in order to remove impurities and then with chloroform/ethanol (89.5:1.5). There is obtained ethyl 6-(2-chlorophenyl)-1,3,4,6-tetrahydro-2-oxo-2H-5,1-benzothiazocine-8-carbamate of melting point 229°-231°.

Workup

  1. additionSubsequently, there are successively added
  2. customat 0° to 2°
  3. customThe cooling means is then removed
  4. customThe mixture is evaporated
  5. customthe residue is chromatographed on 1.44 kg of silica gel
  6. washElution
  7. customto remove impurities

Sources & evidence

ORD record
ord-bbe175b292364e509c7587be1ca35dda
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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