Thionyl Chloride → HCID 178512526, compound

HRID 1709300Notes

Reaction equation

HRID 1709300 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.S(Cl)(Cl)=O.[NH2:30][C:31]1[NH:32][C:33]([Cl:36])=[CH:34][N:35]=1>O1CCCC1.O.C(N(CC)CC)C>[NH:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:30][C:31]2[NH:32][C:33]([Cl:36])=[CH:34][N:35]=2)=[O:11])=[CH:12][CH:13]=1)[C:2]([NH2:4])=[NH:3]

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 11708267BistrimethylsilylacetamidHCID 14819960HCID 14819960, compoundHCID 178512548HCID 178512548, compound

Product 1

HCID 178512526HCID 178512526, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 970 mg. (4.48 m. mol) of 4-guanidinobenzoic acid and 910 mg. (4.48 m. mol) of bis-trimethylsilylacetamide in dry tetrahydrofuran was heated to reflux for five minutes. After cooling the resulting solution of thionylchloride, 1.07 g. (8.95 m. mol) was added, followed after 20 minutes by the addition of 1.5 g. (8.95 m. mol) of 2-amino-5-chloroimidazole and 1.81 g. (17.9 m. mol) of triethyl amine in 10 ml. of tetrahydrofuran. After 16 hours at room temperature 0.40 ml. of water was added and the solids filtered, washed with chloroform and recrystallized from methanol-chloroform-diethyl ether, 435 mg., m.p. 263°-265° C.

Workup

  1. additionA mixture of 970 mg
  2. temperatureto reflux for five minutes
  3. addition(8.95 m. mol) was added
  4. additionfollowed after 20 minutes by the addition of 1.5 g
  5. filtrationthe solids filtered
  6. washwashed with chloroform
  7. customrecrystallized from methanol-chloroform-diethyl ether, 435 mg

Sources & evidence

ORD record
ord-3a90b66550914fe5864e00c8c82ba490
Source dataset
uspto-grants-1990_08
Patent number
US04948891

Reaction notes

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