Hydrochloric Acid → HCID 15228848, compound

HRID 1647087Notes

Reaction equation

HRID 1647087 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=O.B.CSC.CO.Cl>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 19926436HCID 19926436, compound

Product 1

HCID 15228848HCID 15228848, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of the product of Example 1 (25.7 g, 66.1 mmol) in dry tetrahydrofuran (THF, 100 ml) was heated under reflux under an atomosphere of argon, treated dropwise over 25 min with borane-dimethylsulphide (12.5 ml, 131.7 mmol) in THF (100 ml), after 90 min cooled to room temperature, and the suspension treated dropwise with methanol (100 ml), followed by concentrated hydrochloric acid (50 ml). The solution was stirred for 1 h and the precipitate filtered and washed with acetonitrile (20 ml) and ether (3×20 ml) to give the product (15.7 g) m.p. 190°-195°.

Workup

  1. temperatureunder reflux under an atomosphere of argon
  2. filtrationthe precipitate filtered
  3. washwashed with acetonitrile (20 ml) and ether (3×20 ml)

Sources & evidence

ORD record
ord-12547a208e634a738acbbaa62159753a
Source dataset
uspto-grants-1995_07
Patent number
US05430033

Reaction notes

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