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

HRID 1730425Notes

Reaction equation

HRID 1730425 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 702EthanolSolventHCID 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 to7.2), 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 ofethanol. 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 formedis 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. additiondiluting the mixture with 10 ml ofethanol
  4. customAfter 23 hours (and the consumption of about 65% of the theoretical amount of lithium hydroxide) the mixture
  5. washis washed with diethyl ether
  6. filtrationThe precipitate formedis filtered off
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-c909106e3c9a426c9a373e0ac12c008c
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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