Thionyl Chloride → HCID 86753011, compound

HRID 482136Notes

Reaction equation

HRID 482136 reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[C:15]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[S:19][CH2:18][CH2:17][S:16]2)[C:6]([CH3:27])=[N:5][CH:4]=1.S(Cl)([Cl:30])=O>C(Cl)(Cl)Cl>[Cl:30][CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[C:15]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[S:19][CH2:18][CH2:17][S:16]2)[C:6]([CH3:27])=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86753012HCID 86753012, compound

Product 1

HCID 86753011HCID 86753011, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The hydroxy derivative of formula VIII (4 gm) was stirred in 20 ml of chloroform at 0° to 5° C. and to this was added thionyl chloride (2.5 gm) and stirred at 5°-10° C. for 30 minutes, and then for 1 hr. at 20°-25° C. Chloroform was recovered completely and to this was added 20 ml of THF. The precipitated solid was filtered under nitrogen atmosphere and washed well with THF (20 ml). The title compound was obtained as an off-white powder (4.6 gm) as its hydrochloride. Melting point 147°-150° C.; NMR (DMSO, 200 MHz): δ 2.19 (S, 3H, CH3), 3.2-3.5 (m, 4H, S--CH2 ×CH2 --S), 4.5-4.9 (dd, 2H, CH2,Cl) 7.19-8.34 (m, 3H, aromatic-H); IR (KBr): 3500, 1610, 1480, 1100, 780 cm-1.

Workup

  1. waitfor 1 hr
  2. customat 20°-25° C
  3. customChloroform was recovered completely
  4. additionto this was added 20 ml of THF
  5. filtrationThe precipitated solid was filtered under nitrogen atmosphere
  6. washwashed well with THF (20 ml)

Sources & evidence

ORD record
ord-eda0c22a9b2f4731b17b72fadbf46cd5
Source dataset
uspto-grants-1998_08
Patent number
US05792874

Reaction notes

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