Hydrochloric Acid → HCID 23320456, compound

HRID 280441Notes

Reaction equation

HRID 280441 reaction equation
N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([CH3:27])[N:20]=1)=[O:17])(=[O:14])=[O:13].Cl.[N-:29]=[N+:30]=[N-].[Na+]>O>[N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([CH3:27])[N:20]=1)=[O:17])(=[O:14])=[O:13])=[N+:29]=[N-:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23320467HCID 23320467, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23320456HCID 23320456, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1 g of sodium nitrite in 4 ml of water is slowly added dropwise at 0°-5° C. to a mixture of 3.4 g of N-(2-aminophenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea, 10 g of ice and 4 ml of 36% hydrochloric acid. After the reaction mixture has been stirred for 2 hours at 0° C., a solution of 1 g of sodium azide in 4 ml of water is added dropwise and the temperature is allowed to rise to 20° C. The reaction mixture is extracted with three 20 ml portions of methylene chloride. The combined organic phases are dried and concentrated. Recrystallisation of the residue yields 1.0 g of N-(2-azidophenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea which decomposes at 175° C.

Workup

  1. customto rise to 20° C
  2. extractionThe reaction mixture is extracted with three 20 ml portions of methylene chloride
  3. customThe combined organic phases are dried
  4. concentrationconcentrated
  5. customRecrystallisation of the residue

Sources & evidence

ORD record
ord-f8bba0b4dc6347f2b08b0c1b52b4f1a5
Source dataset
uspto-grants-1986_05
Patent number
US04589912

Reaction notes

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