Sulfuric Acid → HCID 23447745, compound

HRID 1840395Notes

Reaction equation

HRID 1840395 reaction equation
O1C2C=CC=CC=2N=C1.NC1C=CC=CC=1.C(OC(=O)[NH:23][CH:24]1[CH2:29][CH2:28][N:27]([S:30]([C:33]2[C:41]3[O:40]C(C(C)(C)C)=[N:38][C:37]=3[CH:36]=[CH:35][C:34]=2[Cl:46])(=[O:32])=[O:31])[CH2:26][CH2:25]1)(C)(C)C.OS(O)(=O)=O>O1CCOCC1.O>[NH2:38][C:37]1[C:41]([OH:40])=[C:33]([S:30]([N:27]2[CH2:26][CH2:25][CH:24]([NH2:23])[CH2:29][CH2:28]2)(=[O:32])=[O:31])[C:34]([Cl:46])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6115AnilineHCID 9228BenzoxazoleHCID 67528166HCID 67528166, compound

Product 1

HCID 23447745HCID 23447745, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Following the general procedure for the hydrolysis of the benzooxazole to the desired aniline outlined in example 51, [1-(2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl)-piperidin4-yl]-carbamic acid tert-butyl ester (4.18 g, 8.86 mmol), water (5.5 mL), and H2SO4 (5.5 mL) in 1,4-dioxane (55mL) were reacted to afford the title compound (2.03 g, 75%). LCMS m/z 306(M−H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-07d062c6f88447c594227f91a3f9536c
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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