Water → HCID 21563685, compound

HRID 1580679Notes

Reaction equation

HRID 1580679 reaction equation
[C:1](Cl)([Cl:3])=[S:2].O.[NH2:6][C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][CH:23]=1)[O:10][C:11]1[N:15]([CH3:16])[C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]=1>O1CCOCC1>[ClH:3].[N:6]([C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][CH:23]=1)[O:10][C:11]1[N:15]([CH3:16])[C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]=1)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10040ThiophosgeneHCID 21563668HCID 21563668, compound

Product 1

HCID 21563685HCID 21563685, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

An amount of 35 g of thiophosgene, 250 ml of dioxane and 100 ml of water is placed into a sulphating flask and cooled to 0° to 5°; an addition is then made dropwise, within 30 minutes, of a solution of 61 g of 2-(3'-aminophenoxy)-1-methylbenzimidazole in 200 ml of dioxane. The mixture is stirred for 3 hours at 0° to 5°; it is afterwards further stirred for 15 hours at room temperature. After dilution with 600 ml of water, the precipitate is separated and stirred, for 7 hours at 10°, into a solution of 10 g of thiophosgene in 500 ml of acetone. The product is separated and recrystallized from acetonitrile to obtain 29.3 g of (3'-isothiocyanophenoxy)-1-methylbenzimidazolehydrochloride, M.P. 154° to 158°C.

Workup

  1. temperaturecooled to 0° to 5°
  2. additionan addition
  3. stirringit is afterwards further stirred for 15 hours at room temperature
  4. customAfter dilution with 600 ml of water, the precipitate is separated
  5. stirringstirred, for 7 hours at 10°, into a solution of 10 g of thiophosgene in 500 ml of acetone
  6. customThe product is separated
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-992bbf66d6254d07ab106b9f68f6d3e8
Source dataset
uspto-grants-1976_01
Patent number
US03933841

Reaction notes

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