Dimethylformamide → HCID 23456164, compound

HRID 1680382Notes

Reaction equation

HRID 1680382 reaction equation
[F:1][S:2]([C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[C:8]([NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:22](O)=[O:23])=[C:16]2[OH:21])=[O:9])(=[O:4])=[O:3].CN(C)C=O.S(Cl)([Cl:35])=O>ClCCl>[F:1][S:2]([C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[C:8]([NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:22]([Cl:35])=[O:23])=[C:16]2[OH:21])=[O:9])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 23456165HCID 23456165, compound

Product 1

HCID 23456164HCID 23456164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

5-(3-Fluorosulphonylbenzamido)-1-hydroxy-2-naphthoic acid (11) (10 g, 26 m.mole) was suspended in dry dichloromethane (200 ml), containing dimethylformamide (0.5 ml) and thionyl chloride (10.8 g, 91 m.mole). The mixture was heated under reflux with stirring for 2.5 hours, during which time the required acid chloride had crystallized as a pale yellow solid. After cooling to 5° C., the acid chloride was removed by filtration and washed with a little cold, dry dichloromethane.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customhad crystallized as a pale yellow solid
  4. customthe acid chloride was removed by filtration
  5. washwashed with a little cold, dry dichloromethane

Sources & evidence

ORD record
ord-6db06deba2304bd791555a66a2aa15b8
Source dataset
uspto-grants-1981_06
Patent number
US04273708

Reaction notes

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