Hydrochloric Acid → HCID 68278000, compound

HRID 931499Notes

Reaction equation

HRID 931499 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH3:3].[ClH:31]>>[ClH:31].[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=3)[O:18][C:19]=2[CH3:20])(=[O:13])=[O:12])=[CH:9][CH:10]=1)[CH3:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68278115HCID 68278115, compound

Product 1

HCID 68278000HCID 68278000, compoundYield 84%

Procedure

A solution of methyl 4-(4-((4-((dimethylamino)methyl)phenylsulfonyl)methyl)-5-methyloxazol-2-yl)benzoate (900 mg, 1.56 mmol, 1.00 equiv, 74%) in 6N hydrochloric acid (25 mL) was refluxed overnight. The resulting solution cooled to room temperature and then diluted with 30 mL of water/ice. The solid was removed by filtration out and washed with 3×20 mL of water. The filtrate and washings were combined and concentrated in vacuum to give 0.6 g (84%) of 4-(4-((4-((dimethylamino)methyl)phenylsulfonyl)methyl)-5-methyloxazol-2-yl)benzoic acid hydrochloride as a yellow solid. LC-MS: (ES, m/z): 415 [M+H]+, 395, 120.

Workup

  1. customThe solid was removed by filtration out and
  2. washwashed with 3×20 mL of water
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-7c20a3daf2734c56a3176292d6483891
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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