Triethylamine → NSC 615985

HRID 1938839Notes

Reaction equation

HRID 1938839 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[O:7][CH2:8][CH2:9][S:10][C:11]=1[C:12]([OH:14])=O.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:28])=[C:20]([CH:27]=1)[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[Cl:28][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:12]([C:11]2[S:10][CH2:9][CH2:8][O:7][C:6]=2[CH3:5])=[O:14])=[CH:27][C:20]=1[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 369590Isopropyl 5-amino-2-chlorobenzoateHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

Product 1

HCID 1385NSC 615985

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (6.5 g, 0.055 mole) was added to a stirring slurry of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (8.0 g, 0.050 mole) in methylene chloride (50 ml). The mixture was stirred at 35°-40° C. for 4 hours, during which the solid completely dissolved. The solution was then evaporated under reduced pressure at about 35° C. to remove hydrogen chloride, sulfur dioxide and unreacted thionyl chloride. The residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, which solidified, was dissolved in methylene chloride (50 ml). The solution was chilled in ice and treated dropwise with a solution of 1-methylethyl 5-amino-2-chlorobenzoate (10.7 g, 0.050 mole) and triethylamine (5.5 g, 0.055 mole) in methylene chloride (50 ml). The addition was carried out over about 2 hours, after which the reaction mixture was left stirring overnight at room temperature.

Workup

  1. dissolutioncompletely dissolved
  2. customThe solution was then evaporated under reduced pressure at about 35° C.
  3. customto remove hydrogen chloride, sulfur dioxide and unreacted thionyl chloride
  4. dissolutionwas dissolved in methylene chloride (50 ml)
  5. temperatureThe solution was chilled in ice
  6. additionThe addition
  7. waitwas carried out over about 2 hours
  8. waitafter which the reaction mixture was left
  9. stirringstirring overnight at room temperature

Sources & evidence

ORD record
ord-7987f601f3104cc7bb05540794462385
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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