Triethylamine → HCID 2799819, compound

HRID 610760Notes

Reaction equation

HRID 610760 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C>ClCCl.Cl>[Cl:17][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 80001Methyl 4-chloroanthranilate

Product 1

HCID 2799819HCID 2799819, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of methanesulphonyl chloride (6.3 g) in dichloromethane was added to a stirred, cooled (0-5° C.) solution of methyl 2-amino-4-chlorobenzoate (9.5 g) in dichloromethane. Triethylamine (7.1 g) was then added and the mixture was stirred at 0-5° C. for 10 minutes and then at room temperature for 0.5 hours. The mixture was diluted with 2N hydrochloric acid. The organic phase was separated, washed with water, dried and evaporated. The crude product was purified by column chromatography to yield methyl 4-chloro-2-(N-methylsulphonylamino)benzoate as a white solid, (3.6 g) m.p. 125.5-128.1° C.

Workup

  1. waitat room temperature for 0.5 hours
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6b11f9e035ad48f59a03328553159e52
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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