Hydrochloric Acid → Isopropyl 2-chloro-5-[(6-methyl-2,3-dihydro-1,4-dithiine-5-carbonyl)amino]benzoate

HRID 326346

Reaction equation

HRID 326346 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[S:11][CH2:10][CH2:9][S:8][C:7]=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].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1.C(Cl)Cl>[Cl:28][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:12]([C:7]2[S:8][CH2:9][CH2:10][S:11][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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 369590Isopropyl 5-amino-2-chlorobenzoateHCID 6005022-Carboxy-3-methyl-5,6-dihydro-1,4-dithiin

Product 1

HCID 503281Isopropyl 2-chloro-5-[(6-methyl-2,3-dihydro-1,4-dithiine-5-carbonyl)amino]benzoateYield 57%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (6.5 g, 0.055 mole) was added slowly to a stirred solution of 5,6-dihydro-3-methyl-1, 4-dithiin-2-carboxylic acid (3 g, 0.017 mole) in toluene (15 ml) at room temperature. The mixture was heated under reflux for 4 hours. The excess toluene and thionyl chloride were removed in a rotary evaporator, yielding the crude acid chloride. 1-Methylethyl 5-amino-2-chlorobenzoate (3 g, 0.014 mole) in pyridine (20 ml) was added slowly to a stirred solution of the crude acid chloride (3 g) in methylene chloride (20 ml) at 20° C. The mixture was stirred for 24 hours, poured onto ice and concentrated hydrochloric acid, washed twice with water, dried with magnesium sulfate, and the methylene chloride evaporated. Recrystallization from 95% ethanol yielded the title compound, m.p. 122°-124° C. (3 g, 57% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe excess toluene and thionyl chloride were removed in a rotary evaporator
  4. customyielding the crude acid chloride
  5. washwashed twice with water
  6. dry with materialdried with magnesium sulfate
  7. customthe methylene chloride evaporated
  8. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-1ba1a775bcdf4435b640ee5cafae3508
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Linked notes

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