Hydrochloric Acid → HCID 178528012, compound

HRID 337377Notes

Reaction equation

HRID 337377 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=2)[NH2:9])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[C:20](N1C=CN=C1)(N1C=CN=C1)=[S:21].Cl>O.CN(C)C=O.ClCCl>[N:9]([C:8]1[CH:7]=[C:6]([C:5]2[NH:1][N:2]=[N:3][N:4]=2)[CH:12]=[CH:11][CH:10]=1)=[C:20]=[S:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 178507542HCID 178507542, compound

Product 1

HCID 178528012HCID 178528012, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The crude 3-(1H-tetrazol-5-yl)aniline was mixed with dichloromethane (15 ml) and cooled to 0° C., and stirred with 2.8 ml (20 mmol) of triethylamine, 2.14 g (12 mmol) of 1,1′-thiocarbonyldiimidazole and N,N-dimethylformamide (5 mL) vigorously at 0° C. for 1 hour. Water (10 ml) was added, and concentrated hydrochloric acid was gradually added dropwise. The light brown solid precipitated at pH 6 to 7 was collected by filtration. Concentrated hydrochloric acid was gradually added dropwise, and the light brown solid precipitated at pH 5 was collected by filtration. The light brown solid was dried under reduced pressure to obtain the desired product (1.31 g, yield 64%, purity 86%).

Workup

  1. customThe light brown solid precipitated at pH 6 to 7
  2. filtrationwas collected by filtration
  3. additionConcentrated hydrochloric acid was gradually added dropwise
  4. customthe light brown solid precipitated at pH 5
  5. filtrationwas collected by filtration
  6. customThe light brown solid was dried under reduced pressure

Sources & evidence

ORD record
ord-ac53b221f2b74731bea86ad4d767e6e4
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

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