Pyridine → HCID 53721476, compound

HRID 2398812Notes

Reaction equation

HRID 2398812 reaction equation
[C:1]([NH:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]21[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>O>[CH3:26][S:27]([O:19][CH:16]1[CH2:17][CH2:18][C:6]2([CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]2[NH:4][C:1](=[O:3])[CH3:2])[CH2:14][CH2:15]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21433508HCID 21433508, compound

Product 1

HCID 53721476HCID 53721476, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of 1.21 g. of 1'-acetamidospiro(cyclohexane-1,2'-indan)-4-ol (isomer B)[27] (prepared in Example 61B) in 12 ml. of pyridine, 1.2 ml. of methane sulfonyl chloride is added. After about 5 hours in the cold the mixture is poured into ice: water. The solid that precipitates is recrystallized from acetone: Skellysolve B to give 1.21 g. of 1'-acetamidospiro(cyclohexane-1,2'-indan-4-ol methanesulfonate (isomer B)[28], melting at 161° to 163° C.

Workup

  1. additionAfter about 5 hours in the cold the mixture is poured into ice
  2. customThe solid that precipitates
  3. customis recrystallized from acetone
  4. customSkellysolve B to give 1.21 g

Sources & evidence

ORD record
ord-079850ae326b4d77893ee99849318cef
Source dataset
uspto-grants-1977_05
Patent number
US04025558

Reaction notes

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