3-Iodo-2-methylprop-1-ene → HCID 54418976, compound

HRID 1576725Notes

Reaction equation

HRID 1576725 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH2:25])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:26][C:27](=[CH2:30])[CH2:28]I>O.[OH-].[Li+].C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:25][CH2:28][C:27]([CH3:30])=[CH2:26])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 108777523-Iodo-2-methylprop-1-eneHCID 54216006HCID 54216006, compound

Product 1

HCID 54418976HCID 54418976, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3939Lithium HydroxideSolvent2×

Procedure

The starting material is prepared as follows: To the solution of 3.81 g of 4-(4-acetamidophenylmercapto)-3-amino-5-sulfamoylbenzoic acid in 25 ml of water and about 2 ml of 4 N aqueous lithium hydroxide (to adjust the pH to 7.2), the solution of 2 g of 2-methylallyliodide in 2 ml of ethanol is added at room temperature while stirring and maintaining the pH between 6.7 and 7.0 with lithium hydroxide, and diluting the mixture with 10 ml of ethanol. After 23 hours (and the consumption of about 65% of the theoretical amount of lithium hydroxide) the mixture is washed with diethyl ether and acidified with hydrochloric acid. The precipitate formed is filtered off and recrystallized from aqueous ethanol, to yield the 4-(4-acetamidophenylmercapto)-3-(2-methylallylamino)-5-sulfamoylbenzoic acid melting at 193°-195°.

Workup

  1. customThe starting material is prepared
  2. additionis added at room temperature
  3. customAfter 23 hours (and the consumption of about 65% of the theoretical amount of lithium hydroxide) the mixture
  4. washis washed with diethyl ether
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-01ee9890bded4591bb22b1b6f4d897e8
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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