2-Chloro-3-nitrobenzoyl chloride → HCID 178522674, compound

HRID 370533Notes

Reaction equation

HRID 370533 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].O.[NH2:15][C:16]1[NH:20][N:19]=[N:18][N:17]=1>O1CCCC1.O>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:15][C:16]1[NH:20][N:19]=[N:18][N:17]=1)=[O:5]

Participants

5

Reactant 2

HCID 126274132-Chloro-3-nitrobenzoyl chlorideHCID 178509300HCID 178509300, compound

Product 1

HCID 178522674HCID 178522674, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Similarly, a solution of 109 g of 2-chloro-3-nitrobenzoyl chloride in 100 ml of tetrahydrofuran was reacted with a mixture of 103 g of 5-aminotetrazole monohydrate in 1200 ml of hot tetrahydrofuran and 50 ml of water. A voluminous precipitate appeared and, after 1 hour, the mixture was diluted with 2 liters of water and the resulting white solid was collected and oven-dried to give 2-chloro-3-nitro-N-(1H-tetrazol-5-yl)-benzamide melting at about 279° C. with decomposition. In this case, the indicated acid chloride was obtained by the reaction of 2-chloro-3-nitrobenzoic acid with phosphorus pentachloride in cyclohexane. The acid chloride melts at about 57°-59° C.

Workup

  1. customthe resulting white solid was collected
  2. customoven-dried

Sources & evidence

ORD record
ord-4ee1abd168c942ab8c48877d05906aa8
Source dataset
uspto-grants-1985_07
Patent number
US04526979

Reaction notes

Loading…