p-Toluenesulfonic acid → 3-Hydroxypropyl 1,3-propanediol 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

HRID 2057662Notes

Reaction equation

HRID 2057662 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[CH2:32]([OH:36])[CH2:33][CH2:34][OH:35].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:27][CH2:26][CH2:25][CH2:24][CH:32]([OH:36])[CH2:33][CH2:34][OH:35].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O-:28])=[O:27])=[CH:30][CH:31]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 20330962Methyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Product 1

HCID 1317118033-Hydroxypropyl 1,3-propanediol 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Procedure

A mixture of 2.25 g. of methyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate, 280 mg. of 1,3-propanediol and 1.37 g. p-toluenesulfonic acid is heated at 180° C. for 18 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield 3-hydroxypropyl 1,3-propanediol 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate.

Workup

  1. additionA mixture of 2.25 g
  2. customis partitioned between ether and 3% aqueous sodium carbonate solution
  3. customThe ether layer is separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-3d6397a869a6488eb049db0e476f0603
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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