Triethylamine → HCID 465805, compound

HRID 326329Notes

Reaction equation

HRID 326329 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][CH2:24][CH2:25][CH3:26])=[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][CH2:24][CH2:25][CH3:26])=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acidHCID 16495765HCID 16495765, compound

Product 1

HCID 465805HCID 465805, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (4.4 g, 0.037 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (5.25 g, 0.033 mole) and methylene chloride (50 ml). The mixture was warmed to a gentle reflux for 3 hours, stirred overnight at room temperature, and evaporated under reduced pressure. The solid residue, crude 5,6-dihydro-2- methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (50 ml), chilled, and treated dropwise over about 2 hours with a solution of propyl 5-amino-2-chlorobenzoate (7.0 g, 0.033 mole) and triethylamine (3.5 g, 0.035 mole) in methylene chloride (50 ml).

Workup

  1. temperatureThe mixture was warmed to
  2. temperaturea gentle reflux for 3 hours
  3. customevaporated under reduced pressure
  4. dissolutionThe solid residue, crude 5,6-dihydro-2- methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (50 ml)
  5. temperaturechilled

Sources & evidence

ORD record
ord-52d987d0042443a59d855fb912352841
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Reaction notes

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