Dimethyl 5-aminoisophthalate → HCID 58880270, compound

HRID 2358198Notes

Reaction equation

HRID 2358198 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21](=[O:33])[C:22]1[CH:31]=[C:30]([NH2:32])[CH:29]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:28][O:27][C:25](=[O:26])[C:24]1[CH:29]=[C:30]([NH:32][S:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:31]=[C:22]([C:21]([O:20][CH3:19])=[O:33])[CH:23]=1

Participants

5

Reactant 2

HCID 66831Dimethyl 5-aminoisophthalateHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Product 1

HCID 58880270HCID 58880270, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-Benzyloxy-benzenesulfonyl chloride (7.35 g, 26.0 mmol) was added in small portions to a suspension of 5-amino isophtalic acid dimethyl ester (5.23 g, 25.0 mmol) in DCM (100 ml) and pyridine (10 ml). The resulting clear yellow solution was stirred for 2 hours at room temperature, the volatile solvents were removed under reduced pressure, the solid residue was suspended in MeOH (125 ml) and the mixture was heated to reflux for 10 minutes. The off white solid was filtered off, washed with water and cold MeOH and dried under high vacuum. Yield 10.93 g (96%).

Workup

  1. customthe volatile solvents were removed under reduced pressure
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 10 minutes
  4. filtrationThe off white solid was filtered off
  5. washwashed with water and cold MeOH
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-6f40729f39394e8396830cb711cee946
Source dataset
uspto-grants-2010_07
Patent number
US07763642B2

Reaction notes

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