Isopropylamine → HCID 22799991, compound

HRID 1438732Notes

Reaction equation

HRID 1438732 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][C@H:7]([C:17]([OH:19])=O)[O:8][C@@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:4]=2[CH:3]=1.S(Cl)(Cl)=O.[NH2:26][CH:27]([CH3:29])[CH3:28]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][C@H:7]([C:17]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:19])[O:8][C@@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 24386Thionyl ChlorideHCID 22799990HCID 22799990, compound

Product 1

HCID 22799991HCID 22799991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A solution of 3.38 g (10.9 mmoles) of trans-6-chloro-4-(2-fluorophenyl)-1,3-benzodioxan-2-carboxylic acid, 10.0 ml (16.4 g, 137 mmoles) of thionyl chloride, and 5 drops of anhydrous DMF in 200 ml of anhydrous Ch2Cl2 was refluxed for 2 hours; the solvent and excess SOCl2 were removed under reduced pressure and the residue was flashed down with 3 portions of anhydrous benzene to remove traces of SOCl2. The acid chloride was redissolved in 100 ml of anhydrous CH2Cl2 and 5.57 ml (3.86 g, 65.4 mmoles) of 2-aminopropane was added all at once; heat was evolved. The reaction mixture stood in a stoppered flask for 16 hours.

Workup

  1. customthe solvent and excess SOCl2 were removed under reduced pressure
  2. customto remove traces of SOCl2
  3. dissolutionThe acid chloride was redissolved in 100 ml of anhydrous CH2Cl2
  4. temperatureheat

Sources & evidence

ORD record
ord-e401c8eb1c414a1fbcfe5128df110156
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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