Hydrochloric Acid → HCID 178528017, compound

HRID 1073475Notes

Reaction equation

HRID 1073475 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:4][CH2:3]1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[S:19].Cl>ClCCl>[N:1]([C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:6][CH2:7]1)=[C:18]=[S:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 802641,1'-ThiocarbonyldiimidazoleHCID 178511509HCID 178511509, compound

Product 1

HCID 178528017HCID 178528017, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 12.2 g of trans-4-(4-aminocyclohexyl)-butylcyclohexane in 135 ml of dichloromethane is added dropwise at 0° under nitrogen to a solution of 15.2 g of 1,1'-thiocarbonyldiimidazole in 90 ml of dichloromethane in the course of 1.5 hours. After standing overnight, about 140 ml of 3% hydrochloric acid are added at 0°-4° until pH 2 is obtained. The organic phase separated off is washed with water until pH 6, is dried over sodium sulfate and evaporated. Purification of the crude product (15.6 g) by column chromatography leaves 13.1 g of trans-4-(4-isothiocyanatocyclohexyl)-butylcyclohexane. Melting point (m.p.) +23°; clear point (c.p.) +72.9°.

Workup

  1. customis obtained
  2. customThe organic phase separated off
  3. washis washed with water until pH 6
  4. dry with materialis dried over sodium sulfate
  5. customevaporated
  6. customPurification of the crude product (15.6 g) by column chromatography

Sources & evidence

ORD record
ord-6d3b982c04a34a2796fb95575d882ebd
Source dataset
uspto-grants-1990_11
Patent number
US04970022

Reaction notes

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